Potassium Carbonate → tert-Butyl methylcarbamate

Participants

Reaction Conditions

Reaction Steps

0.700 g (1.42 mmol) of 3-benzyloxypropyl)triphenylphosphonium bromide, 0.305 g (1.18 mmol) of trans-(4-formyl-cyclohexylmethyl)-methyl-carbamic acid tert-butyl ester (example 1.2) and 0.662 g of finely milled potassium carbonate were suspended in 10.0 ml of 2-methyl-2-butanol and the reaction mixture intensively stirred at 100° C. for 2 hours. It was then evaporated, poured into 50 ml of an ice/water mixture and extracted 3 times with 50 ml of ethylacetate. The combined ethylacetate phases were dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with a 95:5 v/v mixture of dichloromethane and ether as the eluent giving 0.364 g (78.6%) trans-[4-(4-benzyloxy-[E/Z 1:9]but-1-enyl)-cyclohexylmethyl]-methyl-carbamic acid tert-butyl ester as colorless viscous oil, MS: 331 [M−C4H8)+].

Provenance & Evidence