2,6-Lutidine → HCID 178483623, compound

Participants

Reaction Steps

To an ice-cooled solution of 135 mg (0.384 mmol) trans-{2-[4-(3-hydroxy-(E)-propenyl)-cyclohexyl]-ethyl}-methyl-carbamic acid 4-chloro-phenyl ester and 0.089 ml (0.77 mmol) 2,6-lutidine in 2 ml of dichloromethane was added under stirring 0.033 ml (0.422 mmol) methane sulfonylchloride. The reaction mixture was stirred for 20 hours at room temperature, then taken up in ether and washed with 1N hydrogen chloride solution and water. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure and the residue then chromatographed on silica gel with a 4:1 v/v mixture of hexane and ethylacetate as the eluent giving 90 mg (63.4%) of trans-{2-[4-(3-chloro-(E)-propenyl)-cyclohexyl]-ethyl}-methyl-carbamic acid 4-chloro-phenyl ester as colorless viscous oil, MS: 370 (MH+, 2 Cl).

Provenance & Evidence