Triethylamine → HCID 178451163, compound

Participants

Reaction Steps

To a solution of butyl cis-4-(hydroxymethyl)cyclohexanecarboxylate (25.06 g, 117 mmol) and triethylamine (24.3 ml, 17.8 g, 176 mmol) in methylene chloride (600 ml) under nitrogen, cooled in an ice-bath, was added dropwise over 20 minutes methane-sulfonyl-chloride (13.6 ml, 16.1 g, 140 mmol). The solution was stirred 18 hours while warming from 0° C. to ambient temperature. Additional triethylamine (2 ml, 1.5 g, 14 mmol) and methane-sulfonyl-chloride (1 ml, 1.5 g, 13 mmol) were added and the mixture was stirred four hours at ambient temperature. The mixture was diluted with methylene chloride (300 ml), washed with IN hydrochloric acid (300 ml), water (300 ml), and half-saturated sodium carbonate solution (300 ml), dried (sodium sulfate), filtered, and the solvent was evaporated under reduced pressure to give crude butyl cis-4-{[(methylsulfonyl)oxy]methyl}cyclohexanecarboxylate (35.31 g) as an orange oil: 1H NMR (CDCl3) 4.08 (4H, m), 3.00 (3H, s), 2.59 (1H, m), 2.05 (2H, m), 1.86 (1H, m) 1.52-1.69 (6H, m), 1.31-1.43 (4H, m), 0.94 (3H, m). MS.: 293.3 (M+1).

Provenance & Evidence