2-Furanmethanethiol → HCID 53773593, compound

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Reaction Steps

Using, in the process of example 14, ethyl 3-cyclohexyl-2-ethoxycarbonyl-propionate and 2-trityloxyethyl bromide, 4-cyclohexyl-2,2-diethoxycarbonyl-butan-1-ol is obtained and then by reaction in dichloromethane with triphenylphosphine and tetrabromomethane, 4-cyclohexyl-2,2-diethoxy-1-butyl-bromide. A solution of 0.1 g of potassium tert-butylate in 6 ml of THF/EtOH 1:2 is added with 0.15 g of furfurylmercaptan and 0.38 g of 4-cyclohexyl-2,2-diethoxy-1-butyl bromide. The mixture is refluxed for 4 hours under nitrogen atmosphere, evaporated and partitioned between AcOEt and water. After the usual work up, the solvent is evaporated off and the residue is purified on a silica gel column, to obtain 0.34 g of ethyl 4-(fur-2-ylmethylthio)-2-ethoxycarbonyl-2-cyclohexylmethyl-butanoate.

Provenance & Evidence