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Reaction information
*#Reaction file | Scheme_312.cdx |
*Reaction file type | CDX |
*Procedure |
To a stirring solution of N-benzyl-N-(3-heptynyl)amine (309, 1.0 g, 4.8 mmol), K2CO3 (1.2 g, 12.0 mmol) and MeCN (10.0 mL), benzenesulfonate (307, 1.33 g, 5.0 mmol) was added dropwise. The reactants were refluxed for 24 hrs then quenched using NaOH (6M, 30.0 mL). The product was extracted into diethyl ether (3 x 100 mL), the combined organic layer washed with water (3 x 100 mL), brine (50.0 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure. Column chromatography (SiO2, 0-100 % Et2O:petroleum including 5 % Et3N) afforded the title compound as a viscous clear oil (1.3 g, 4.4 mmol, 88 %). |
*Yield (%) | 88 |
*Type of Yield | Isolated product yield |
Reference(s) | DM Thesis_2000_pp40-49.pdf DM Thesis_2000_pp106.pdf |
Further information |
For multistep reactions (or their steps):
Overall reaction? | True |
For overall reaction - links to child reaction steps | |
For step in multistep reaction - link to previous reaction step | |
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Reaction information
*#Reaction file | CSRxnsScheme_136b.cdx |
*Reaction file type | CDX |
*Procedure |
General procedure C (see below) with N-(Dec-9-en-3-yn-1-yl)-N-(hex-1-yn-1-yl)-4-methylbenzenesulfonamide (372 mg, 1.0 mmol). Purification by column chromatography (SiO2, hexane/Et2O 9:1) gave the title compound as the minor product as a pale yellow oil (119 mg, 32%).
The minor product was (E)‑N‑(hex‑1‑yn‑1‑yl)‑4‑methyl‑N‑(3‑(2‑methylcyclohexylidene)propyl)benzenesulfonamide (136b) obtained as a pale yellow oil (102 mg, 26%).
General procedure C: zirconocene mediated cocyclisation of ynamides n-BuLi (0.88 mL of a 2.5 M solution in hexanes, 2.2 mmol) was added dropwise to a solution of Cp2ZrCl2 (322 mg, 1.1 mmol) in dry THF (5.0 mL) at −78 °C. A solution of the appropriate ynamide (1.0 mmol) in dry THF (3.0 mL) was added dropwise at −78 °C. The reaction mixture was warmed to room temperature and stirred for 5 h. The reaction mixture was cooled to −78 °C and MeOH (10.0 mL) added. After stirring at −78 °C for 1 h the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was poured into water (100 mL) and extracted with ether (3 × 50 mL). The organic extracts were combined, washed sequentially with water (2 × 100 mL) and brine (100 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product, which was purified as described. |
*Yield (%) | 26 |
*Type of Yield | Isolated product yield |
Reference(s) | AH Thesis_2011_pp106.pdf AH Thesis_2011_pp176-223.pdf |
Further information | Compound 136b: (E)‑N‑(hex‑1‑yn‑1‑yl)‑4‑methyl‑N‑(3‑(2‑methylcyclohexylidene)propyl)benzenesulfonamide |
For multistep reactions (or their steps):
Overall reaction? | True |
For overall reaction - links to child reaction steps | |
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For step in multistep reaction - link to following reaction step |
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Reaction information
*#Reaction file | CSRxnsScheme_135b.cdx |
*Reaction file type | CDX |
*Procedure |
General procedure C (see below) with N-(Dec-9-en-3-yn-1-yl)-N-(hex-1-yn-1-yl)-4-methylbenzenesulfonamide (372 mg, 1.0 mmol). Purification by column chromatography (SiO2, hexane/Et2O 9:1) gave the title compound as the minor product as a pale yellow oil (119 mg, 32%).
General procedure C: zirconocene mediated cocyclisation of ynamides n-BuLi (0.88 mL of a 2.5 M solution in hexanes, 2.2 mmol) was added dropwise to a solution of Cp2ZrCl2 (322 mg, 1.1 mmol) in dry THF (5.0 mL) at −78 °C. A solution of the appropriate ynamide (1.0 mmol) in dry THF (3.0 mL) was added dropwise at −78 °C. The reaction mixture was warmed to room temperature and stirred for 5 h. The reaction mixture was cooled to −78 °C and MeOH (10.0 mL) added. After stirring at −78 °C for 1 h the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was poured into water (100 mL) and extracted with ether (3 × 50 mL). The organic extracts were combined, washed sequentially with water (2 × 100 mL) and brine (100 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product, which was purified as described. |
*Yield (%) | 32 |
*Type of Yield | Isolated product yield |
Reference(s) | AH Thesis_2011_pp106.pdf AH Thesis_2011_pp176-223.pdf |
Further information | Compound 135b: (2Z,3E)-3-(Hept-6-en-1-ylidene)-2-pentylidene-1-tosylpyrrolidine |
For multistep reactions (or their steps):
Overall reaction? | True |
For overall reaction - links to child reaction steps | |
For step in multistep reaction - link to previous reaction step | |
For step in multistep reaction - link to following reaction step |
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Reaction information
*#Reaction file | CSRxnsScheme_136a.cdx |
*Reaction file type | CDX |
*Procedure |
General procedure C (see below) with N-(Hex-1-yn-1-yl)-4-methyl-N-(non-8-en-3-yn-1-yl)benzenesulfonamide (372 mg, 1.0 mmol). Purification by column chromatography (SiO2, hexane/Et2O 9:1) gave the product as a pale yellow oil (119 mg, 32%). The major product (title compound) was (E)‑N‑(hex‑1‑yn‑1‑yl)‑4‑methyl‑N‑(3‑(2‑methylcyclopentylidene)propyl)benzenesulfonamide (136a) obtained as a pale yellow oil (150 mg, 40%)
General procedure C: zirconocene mediated cocyclisation of ynamides n-BuLi (0.88 mL of a 2.5 M solution in hexanes, 2.2 mmol) was added dropwise to a solution of Cp2ZrCl2 (322 mg, 1.1 mmol) in dry THF (5.0 mL) at −78 °C. A solution of the appropriate ynamide (1.0 mmol) in dry THF (3.0 mL) was added dropwise at −78 °C. The reaction mixture was warmed to room temperature and stirred for 5 h. The reaction mixture was cooled to −78 °C and MeOH (10.0 mL) added. After stirring at −78 °C for 1 h the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was poured into water (100 mL) and extracted with ether (3 × 50 mL). The organic extracts were combined, washed sequentially with water (2 × 100 mL) and brine (100 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product, which was purified as described. |
*Yield (%) | 40 |
*Type of Yield | Isolated product yield |
Reference(s) | AH Thesis_2011_pp106.pdf AH Thesis_2011_pp176-223.pdf |
Further information | Compound 136b: (E)‑N‑(hex‑1‑yn‑1‑yl)‑4‑methyl‑N‑(3‑(2‑methylcyclohexylidene)propyl)benzenesulfonamide |
For multistep reactions (or their steps):
Overall reaction? | True |
For overall reaction - links to child reaction steps | |
For step in multistep reaction - link to previous reaction step | |
For step in multistep reaction - link to following reaction step |
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See ChemSpider Reactions template - help and further information for help when using it.
Reaction information
*#Reaction file | CSRxnsScheme_135a.cdx |
*Reaction file type | CDX |
*Procedure |
General procedure C (see below) with N-(Hex-1-yn-1-yl)-4-methyl-N-(non-8-en-3-yn-1-yl)benzenesulfonamide (372 mg, 1.0 mmol). Purification by column chromatography (SiO2, hexane/Et2O 9:1) gave the title compound as the minor product as a pale yellow oil (119 mg, 32%).
General procedure C: zirconocene mediated cocyclisation of ynamides n-BuLi (0.88 mL of a 2.5 M solution in hexanes, 2.2 mmol) was added dropwise to a solution of Cp2ZrCl2 (322 mg, 1.1 mmol) in dry THF (5.0 mL) at −78 °C. A solution of the appropriate ynamide (1.0 mmol) in dry THF (3.0 mL) was added dropwise at −78 °C. The reaction mixture was warmed to room temperature and stirred for 5 h. The reaction mixture was cooled to −78 °C and MeOH (10.0 mL) added. After stirring at −78 °C for 1 h the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was poured into water (100 mL) and extracted with ether (3 × 50 mL). The organic extracts were combined, washed sequentially with water (2 × 100 mL) and brine (100 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product, which was purified as described. |
*Yield (%) | 32 |
*Type of Yield | Isolated product yield |
Reference(s) | AH Thesis_2011_pp106.pdf AH Thesis_2011_pp176-223.pdf |
Further information | Compound 135a: (2Z,3E)-3-(Hex-5-en-1-ylidene)-2-pentylidene-1-tosylpyrrolidine |
For multistep reactions (or their steps):
Overall reaction? | True |
For overall reaction - links to child reaction steps | |
For step in multistep reaction - link to previous reaction step | |
For step in multistep reaction - link to following reaction step |