Characterization Template - Proton NMR
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This post is compatible for submission to ChemSpider Reactions.
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Reaction information
*#Reaction file | OverallReactionScheme.cdx |
*Reaction file type | CDX |
*Procedure | See Child Reaction Steps |
*Yield (%) | N/A |
*Type of Yield | N/A |
Reference(s) | Thesis L Sayer10-11.pdf |
Further information | - |
For multistep reactions (or their steps):
Overall reaction? | True |
For overall reaction - links to child reaction steps | Reaction 73 Reaction 32 |
For step in multistep reaction - link to previous reaction step | N/A |
For step in multistep reaction - link to following reaction step | N/A |
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Reaction information
*#Reaction file | OverallReaction.cdx |
*Reaction file type | CDX |
*Procedure | See Child Reaction Steps |
*Yield (%) | N/A |
*Type of Yield | N/A |
Reference(s) | DavidOwenThesis2000pp82,83,171,172.pdf |
Further information | Compound 430: 7-[4,4-Di(methoxymethyl)-2-methylcyclopentyl]-1-heptanol |
For multistep reactions (or their steps):
Overall reaction? | True |
For overall reaction - links to child reaction steps | Reaction 429 Reaction 430 |
For step in multistep reaction - link to previous reaction step | N/A |
For step in multistep reaction - link to following reaction step | N/A |
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Reaction information
*#Reaction file | ReactionScheme.cdx |
*Reaction file type | CDX |
*Procedure |
To a solution of tert-butyl[2-(2-{(E)-4-[4,4-di(methoxymethyl)-2-methylcyclo pentyl]-2-butenyl}-1,3-dithian-2-yl)ethoxy]dimethylsilane (117 mg, 0.23 mmol) in THF (3 mL) was added dropwise tetrabutyl ammonium fluoride (0.35 mL of a 1 M solution in THF, 0.35 mmol). The mixture was stirred for 1 h, before being quenched with water (5 mL). The solution was diluted with ether, and the aqueous phase extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. To the crude product was added ethanol (5 mL) and Raney nickel (10 g of a 1:1 slurry in water). The mixture was heated at reflux for 2 h, then filtered through a sinter, with ether and water washing. The phases of the filtrate were separated and the aqueous extracted with ether. The combined extracts were washed with brine, dried over MgSO4 and concentrated. Purification of the crude product by column chromatography (SiO2, 20% ether in petrol) yielded the title compound (31 mg, 0.11 mmol, 47%). |
*Yield (%) | 47 |
*Type of Yield | Isolated Product Yield |
Reference(s) | DavidOwenThesis2000pp82,83,171,172.pdf |
Further information | Compound 430: 7-[4,4-Di(methoxymethyl)-2-methylcyclopentyl]-1-heptanol |
For multistep reactions (or their steps):
Overall reaction? | False |
For overall reaction - links to child reaction steps | N/A |
For step in multistep reaction - link to previous reaction step | Reaction 429 |
For step in multistep reaction - link to following reaction step | N/A |
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Reaction information
*#Reaction file | ReactionScheme.cdx |
*Reaction file type | CDX |
*Procedure |
n-Butyllithium (0.21 mL of a 2.5 M solution in hexanes, 0.525 mmol) was added dropwise to a solution of 2-{(E)-4-[4,4-di(methoxymethyl)-2-methylcyclopentyl]-2-butenyl}-1,3-dithiane (427) in THF (3 mL) under Ar at –40 °C. The reaction was stirred for 2 h and allowed to warm to –20 °C. After cooling to –78 °C, HMPA (0.2 mL) was added, resulting in a bright yellow suspension, which was decolourised on addition of a solution of (2-iodoethoxy)-tert-butyl dimethyl silane (143 mg, 0.5 mmol) in THF (1 mL). After 30 min, the solution was allowed to warm to room temperature and stirred over night. The reaction mixture was poured into water and ether, and the aqueous layer extracted with ether. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated. Column chromatography (SiO2, 10% ether in petrol) furnished the desired compound as a viscous, colourless oil (141 mg, 0.28 mmol, 56%) contaminated with a small amount of an inseparable impurity. |
*Yield (%) | 56 |
*Type of Yield | Reaction Yield |
Reference(s) | DavidOwenThesis2000pp82,83,170,171.pdf 429LABBOOK.JPG |
Further information | Compound 429: tert-Butyl[2-(2-{(E)-4-[4,4-di(methoxymethyl)-2-methylcyclopentyl]-2-butenyl}-1,3-dithian-2-yl)ethoxy]dimethylsilane |
For multistep reactions (or their steps):
Overall reaction? | False |
For overall reaction - links to child reaction steps | N/A |
For step in multistep reaction - link to previous reaction step | N/A |
For step in multistep reaction - link to following reaction step | Reaction 430 |
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Reaction information
*#Reaction file | ReactionScheme.cdx |
*Reaction file type | CDX |
*Procedure | Ethylene oxide (1 mL of 1:1 solution in ether, 10 mmol) was added to a solution of TBDMSCl (1.507 g, 10 mmol) and NaI (1.5 g, 10 mmol) in MeCN (1.5 mL) under Ar at 0 oC. After an hour the solution was poured into H2O and ether. Extracted into ether/pentane. The extracts were washed with Na2S2O3 and brine. Then it was dried over MgSO4 and concentrated. The crude product was then columned (20% ether) to produce the desired compound (1.196 g, 42%) |
*Yield (%) | 42 |
*Type of Yield | Reaction Yield |
Reference(s) | DavidOwenThesis2000pp82,83,170.pdf |
Further information | Compound 428: (2-Iodoethoxy)-tert-butyldimethylsilane |
For multistep reactions (or their steps):
Overall reaction? | True |
For overall reaction - links to child reaction steps | N/A |
For step in multistep reaction - link to previous reaction step | N/A |
For step in multistep reaction - link to following reaction step | N/A |