Diethyl Ether → HCID 131717628, compound

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Reaction Steps

Commercially available (1S,5S,6S,7R)-6-(t-butyldimethylsiloxymethyl)-3-formyl -7-tetrahydropyranyloxybicyclo[3.3.0]oct-2-ene (1.00 g) (1) was reacted with an ylide which was prepared from (3-carboxypropyl)triphenylphosphine bromide and potassium t-butoxide. A crude carboxylic acid was obtained according to a usual work-up. The product was reacted with diazomethane in ether. A crude product obtained after a usual work-up was purified on a column chromatography (hexane/ethyl acetate=10/1) to give (1S,5S,6S,7R)-6-(t-butyldimethylsiloxymethyl)-3-[4-methoxycarbonyl-1(EZ)-butenyl]-7-tetrahydropyranyloxybicyclo[3.3.0]oct-2-ene (2) as a colorless oily product. Yield: 0.85 g (67%)

Provenance & Evidence