Triethylamine → HCID 19801120, compound

Participants

Reaction Steps

In dimethylformamide (0.5 ml) were dissolved 2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-1-(2-hydroxymethylbenzyl)thiomethyl-3-methoxy-1,4cyclohexanediol (100 mg) and triethylamine (64 μl). To the solution was added, under ice-cooling, lithium chloride (21 mg). To the mixture was added dropwise methanesulfonyl chloride (20 μl), which was stirred for hours, then the reaction was suspended by the addition of water. The product was extracted with ether, and the extract solution was washed with a saturated aqueous solution of sodium chloride, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by means of a silica gel column chromatography (carrier 10 g, developing solvent : ethyl acetate - hexane=1:2) to give 1-(2-chloromethylbenzyl)thiomethyl-2 -(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1,4-cyclohexanediol (70 mg: yield 67%) as a colorless oily product.

Provenance & Evidence