Characterization Template - Proton NMR
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Reaction information
*#Reaction file | reactionscheme_40d.cdx |
*Reaction file type | CDX |
*Procedure |
To a 30 mL Schlenk vial under argon at room temperature was added dppf (68.1 mg, 0.13 mmol), sodium propane-2-thiolate (0.51 g, 5.0 mmol), PhBr (0.21 g, 1.3 mmol) and BnNC (0.22 mL, 2.0 mmol). PdCl2 (12.8 mg, 0.072 mmol) was then added against a counterflow of argon. Finally, toluene (13 mL) was used to wash all solids from the sides of the vial, which was then heated at 109 °C in a Stem block. The reaction mixture was allowed to cool to room temperature before ether (10 mL) and concentrated aqueous potassium hydroxide solution (5 mL) were added. The aqueous layer was extracted with ether (3x15 mL). The combined organics were dried over MgSO4, filtered and evaporated. Further purification on silica with petrol:ether (4:1) gave the title compound as a pale-yellow oil, (0.13 g, 40%), found to consist of two isomers by NMR in a ratio of 1 : 2. |
*Yield (%) | 40 % |
*Type of Yield | Isolated pure product |
Reference(s) | Gustaf Saluste p122-123.pdf |
Further information |
For multistep reactions (or their steps):
Overall reaction? | True |
For overall reaction - links to child reaction steps | |
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Reaction information
*#Reaction file | reactionscheme_40c.cdx |
*Reaction file type | CDX |
*Procedure |
To a 30 mL Schlenk vial under argon at room temperature was added dppf (66.8 mg, 0.13 mmol), sodium propane-2-thiolate (0.50 g, 5.0 mmol), PhBr (0.20 g, 1.3 mmol) and n-BuNC (0.20 mL, 2.0 mmol). PdCl2 (12.5 mg, 0.072 mmol) was then added against a counterflow of argon. Finally, toluene (13 mL) was used to wash all solids from the sides of the vial, which was then heated at 109 °C in a Stem block for 5 h. The reaction mixture was allowed to cool to room temperature before ether (10 mL) and concentrated aqueous potassium hydroxide solution (5 mL) were added. The aqueous layer was extracted with ether (3x15 mL). The combined organics were dried over MgSO4, filtered and evaporated. Further purification on silica with petrol:ether (2:1) gave the title compound as a pale-yellow oil, (0.19 g, 62%), found to consist of two isomers in a ratio of 3.7 : 1 by NMR. |
*Yield (%) | 62 % |
*Type of Yield | Isolated pure product |
Reference(s) | Gustaf Saluste p121-122.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 | |
For step in multistep reaction - link to following reaction step |
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Reaction information
*#Reaction file | overallscheme_31b.cdx |
*Reaction file type | CDX |
*Procedure | See child reaction steps |
*Yield (%) | |
*Type of Yield | |
Reference(s) | Gustaf Saluste p106-107.pdf |
Further information |
For multistep reactions (or their steps):
Overall reaction? | True |
For overall reaction - links to child reaction steps |
Reaction 31B: Synthesis by tert-butyl deprotection of phenyl(tetrahydro-1H-1-pyrrolyl)methanimine |
For step in multistep reaction - link to previous reaction step |
|
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Reaction information
*#Reaction file | reactionscheme_33i (2).cdx |
*Reaction file type | CDX |
*Procedure |
Dry Cs2CO3 (0.81 g, 2.5 mmol), dppf (0.11 g, 0.20 mmol),4-bromoacetophenone (0.40 g, 2.0 mmol) and morpholine (0.73 g, 0.010 mol) were added to a 30 mL Schlenk tube under argon. Dry, de-gassed toluene (10 mL) was added, followed by tBuNC (0.34 mL, 3.0 mmol) and finally PdCl2 (19.8 mg, 0.11 mmol) was added against a flow of argon. Another aliquote of toluene (10 mL) was added and the tube fitted with a stopper. The mixture was heated with stirring at 109 °C for 5 h. After cooling to room temperature, the reaction mixture was added to ether (20 mL) and the resulting slurry was filtered and extracted with dilute acetic acid (2.5% in water, 6x5 mL). The combined aqueous extractions were washed with ether (2x10 mL), then treated with a concentrated KOH-solution (30 mL) in presence of ether (20 mL). The ethereal layer was collected and the aqueous layer extracted with ether (3x30 mL). The combined ether phases were dried over MgSO4 before evaporation. Work-up followed by Kugelrohr-distillation gave the title compound as yellow crystals, (0.35 g, 62%), m.p. 102-104 oC. |
*Yield (%) | 62 % |
*Type of Yield | Isolated pure product |
Reference(s) | Gustaf Saluste p98.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 | |
For step in multistep reaction - link to following reaction step |
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Reaction information
*#Reaction file | reactionscheme_32i(1).cdx |
*Reaction file type | CDX |
*Procedure |
Dry Cs2CO3 (0.84 g, 2.6 mmol), dppf (0.11 g, 0.20 mmol), 3-bromopyridine (0.32 g, 2.0 mmol) and pyrrolidine (0.73 g, 0.011 mol) were added to a 30 mL Schlenk tube under argon. Dry, de-gassed toluene (10 mL) was added, followed by tBuNC (0.34 mL, 3.0 mmol) and finally PdCl2 (19.6 mg, 0.11 mmol) was added against a flow of argon. Another aliquote of toluene (10 mL) was added and the tube fitted with a stopper. The mixture was heated with stirring at 109 °C for 5 h. After cooling to room temperature, the reaction mixture was added to ether (20 mL) and the resulting slurry filtered to give a dark-brown solution which was extracted with dilute acetic acid (2.5% in water, 6x5 mL). The combined aqueous extractions were washed with ether (2x10 mL), then treated with a concentrated KOH-solution (30 mL) in presence of ether (20 mL). The ethereal layer was collected and the aqueous layer extracted with ether (3x30 mL). The combined ether phases were dried over MgSO4 before evaporation. Kugelrohr-distillation (oven temp 105-110 oC / 1 mmHg) gave the title compound as a transparent oil which crystallised in the freezer to give a white solid, (0.33 g, 71%), m.p. 28-30 oC |
*Yield (%) | 71 % |
*Type of Yield | Isolated pure product |
Reference(s) | Gustaf Saluste p92-93.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 | |
For step in multistep reaction - link to following reaction step |