Acetic Acid → 1-[3-(tert-butyldimethylsilyloxymethyl)-phenyl]-(1E)-undecen-3-ol

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Reaction Steps

483 mg of sodium borohydride is added to a solution of 6.5 g of the above-produced ketone in 270 ml of methanol under argon at 0° C. and stirred for one hour at this temperature. Then, it is mixed with 1.5 ml of glacial acetic acid, diluted with 150 ml of water and extracted three times with 200 ml of ethyl acetate each. The organic phase is washed neutral with brine, dried on magnesium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel. With hexane/0-20% ethyl acetate, 5.65 g of 1-[3-(tert-butyldimethylsilyloxymethyl)-phenyl]-(1E)-undecen-3-ol is obtained as colorless oil.

Provenance & Evidence