Potassium bisulfate → HCID 178486039, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 4.5 g (16.8 mmol) of trans-[4-(3-Hydroxy-prop-1-ynyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester in 180 ml Et2O was cooled (0° C.) and treated slowly with a solution of 13.46 ml (47.1 mmol) of Red-Al (70% in toluene). The solution was stirred 2 h at RT, cooled (0° C.) and treated again with 1.3 ml (4.7 mmol) of Red-Al (70% in toluene). After 2 h at RT, the reaction was cooled (−50° C.) and hydrolyzed with a suspension of 3 g MgSO4.7H2O, 3 g silicagel in 4 ml aqueous 10% KHSO4. The cooling bath was removed, THF was added, the mixture was filtered. After evaporation, the residue was dissolved in CH2Cl2, dried over Na2SO4 and evaporated to yield 3.59 g (quantitative) of trans-(1E)-[4-(3-Hydroxy-propenyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester, MS: 270 (MH+).

Provenance & Evidence