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16th September 2013 @ 13:47

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Reaction information

*#Reaction file
*Reaction file type CDX

To a stirred solution of 3-((3aR,6aS)-2-hexyl-6a-(1-phenylvinyl)-3,3a,4,5,6,6a-hexahydropentalen-1-yl)propan-1-ol (50 mg, 0.14 mmol, 1 equiv.) in THF (5 mL) was added at 0 °C sodium hydride (95 %, 8 mg, 0.28 mmol, 2 equiv.).  The reaction was stirred at room temperature for 1 hour, before dropwise addition of tert-butyl bromoacetate (33 mg, 0.17 mmol, 1.5 equiv.).  The reaction was refluxed overnight.

The reaction was quenched with ammonium chloride solution (sat. aq., 12 mL) and poured onto water (10 mL).  The product was extracted into diethyl ether (3 x 10 mL) and washed with water (3 x 20 mL) before being dried over magnesium sulphate, filtered and concentrated under reduced pressure.

The product was purified by column chromatography (silica gel, 7% diethyl ether in petroleum ether) to yield the pure product (31 mg, 0.07 mmol, 48 %) as a colourless oil. 

*Yield (%) 48
*Type of Yield Isolated Product Yield
Further information -

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 10 
For step in multistep reaction - link to following reaction step Reaction 65
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