Sodium Chloride → HCID 12795072, compound

Participants

Reaction Steps

Triethylamine (31 g, 0.306 moles) and methanesulfonyl chloride (32 g, 0.279 moles) are successively added to a stirred and cooled (-8°) solution of 1-(3-hydroxypropyl)pyrrol-2-acetonitrile (38.1 g., 0.232 moles) in dichloromethane (250 ml.), maintained in an atmosphere of nitrogen, at a rate such that the reaction temperature did not exceed 0°. After a further 1 hour at this temperature (t.l.c. silica gel, dichloromethane-acetone, 95:5), saturated sodium becarbonate solution (4.4 ml.), saturated sodium chloride solution (45 ml.) and water (50 ml.) is added. The mixture is stirred for 5 min., the organic phase is separated, and combined with the dichloromethane extracts (2×100 ml.) of the aqueous phase. The extract is washed successively with saturated sodium bicarbonate solution (25 ml.), saturated sodium chloride solution (50 ml.) and water (50 ml.), and then dried over sodium sulfate. The solvent was removed in vacuo and the residual oil (77 g) is purified by chromatography on silica gel to give 42.7 g of 1-(3-methansul-fonyloxypropyl)pyrrol-2-acetonitrile (Formula (XVIII) where n is 1), (76%) was contained in the fraction eluted with hexane-dichloromethane (90:10). This product has the following physical characteristics:

Provenance & Evidence