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16th September 2013 @ 13:56

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Reaction information

*#Reaction file
ReactionScheme.cdx
 
*Reaction file type CDX 
*Procedure

To a stirred solution of (3-(1-((3aR,6aR)-5-hexyl-4-phenyl-1,2,3,3a,6,6a-hexahydropentalen-3a-yl)vinyl)phenyl)methanol (0.10 g, 0.24 mmol, 1 equiv.) in DMF (1 mL) at 0°C was added NaH (95%, 0.024 g, 0.96 mmol, 4 equiv.).  The reaction was warmed to room temperature and stirred for 2 hours.  t-Butyl bromoacetate (0.7 mL, 0.48 mmol, 2 equiv.) was added dropwise at 0°C and the reaction was stirred at room temperature overnight.

The reaction was quenched with ammonium chloride solution (sat., aq., 2 mL) and the product extracted into diethyl ether (3 x 5 mL).  The organic layers were combined and washed with water (3 x 20 mL) before being dried over magnesium sulphate, filtered and concentrated under reduced pressure to give the crude product.

The product was purified by column chromatography (silica gel, 4% diethyl ether in cyclohexane) to yield the pure product (95 mg, 0,18 mmol, 77%). 

*Yield (%) 77
*Type of Yield Isolated Product Yield 
Reference(s)
L.Sayerpp36.pdf
 
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 38 
For step in multistep reaction - link to following reaction step Reaction 70
Attached Files
ReactionScheme.cdx
L.Sayerpp36.pdf