PMGB

chemical reaction procedures

Dialkyl ether

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To a suspension of sodium hydride (0.0004 mol) and alkyl methanesulfonate (0.0004 mol) in 5 mL THF at ice-bath temperature was added benzyl alcohol (0.0004 mol) in 5 mL THF dropwise. After the addition was complete, the resulting reaction mixture was allowed to warm to room temperature and then heated at 50 oC for 12 h. The reaction mixture was evaporated, diluted with 50 mL ethyl acetate, washed with saturated aq. NaHCO3 solution and brine, dried (Na2SO4) and evaporated to give the corresponding benzyl alkyl ether  which was purified by silica gel column chromatography using ethyl acetate (75% yield, NMR and MS complies).

Procedure was taken from Bhatia S. K.; Hajdu, J. J. Org. Chem. 1988, 53, 5034-5039.

Note: This procedure worked in the presence of lactam and piperazine moieties.

Written by pmgb

May 19, 2008 at 5:37 am

Posted in alcohols, ethers, mesylates

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