Dimethylformamide → 3-(5-Methoxymethoxy-4,6,7-trimethyl-1,3-benzoxathiole-2-yl)propanol

Participants

Reaction Steps

340 mg of a 55% w/w oily suspension of sodium hydride was added to 20 ml of dimethylformamide, followed by 2.0 g of crystals of 3-(5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiole-2-yl)propanol (prepared as described in Example 71), with ice cooling and under a stream of nitrogen. The reaction mixture was then cooled with ice for 30 minutes, after which it was allowed to react for 1 hour at room temperature; it then was again cooled with ice. A solution of 630 mg of chloromethyl methyl ether in 2 ml of benzene was then added dropwise, after which the temperature of the reaction mixture was gradually raised and the reaction mixture was allowed to react further for 20 hours at room temperature. The reaction mixture was then poured into water and extracted with benzene. The extract was washed with water and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was subjected to silica gel Lobar column chromatography. The title compound was obtained from the fraction eluted with a 9:1 by volume mixture of benzene and ethyl acetate.

Provenance & Evidence