Acetone → HCID 12795056, compound

Participants

Reaction Steps

Dimethyl sulfate (44.2 g, 0.362 moles) is added to a stirred and cooled solution of 1-(3-hydroxypropyl)-2-dimethylaminopyrrole (57 g, 0.313 moles) in acetone (285 ml), maintained in an atmosphere of nitrogen, at a rate such that the reaction temperature does not exceed 4° C. The reaction is then allowed to come to room temperature at which point stirring is continued for a further 1 hour. The reaction is complete (t.l.c., silica gel, CH2Cl2 --MeOH; 90:10) at this time and a solution of sodium cyanide (33.4 g., 1.28 moles) in water (74 ml.) is added. The apparatus is equipped to permit distillation and the reaction is heated to 95° during which time a distillate (ca. 275 ml.) is collected. The reaction is then heated at gentle reflux for 0.5 hours and 150 ml. water is added. the product is extracted into dichloromethane (4×200 ml.), the extract is washed with dilute sodium chloride solution and then dried over sodium sulfate. The solvent is removed in vacuo and the oily residue (51 g) is purrified by column chromatography over silica gel to give 38.1 g (74%) 1-(3-hydroxypropyl)pyrrol-2-acetonitrile (Formula (XVII) where n is 1) which is contained in the hexane-ethyl acetate (85:15) eluate. The product on distillation, b.p. 146°/0.15 mm is analytically pure and exhibited the following physical characteristics:

Provenance & Evidence