Ethyl orthoformate → 4-(2-Hydroxyethyl)-3,5-dimethyl-1H-pyrrole-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-(2-acetoxyethyl)-3,5-dimethylpyrrole-2-carboxylate (15 g, 53 mmol) was dissolved in TFA (40 ml) and the solution was stirred at 40° C. under nitrogen for 10 min. The reaction mixture was then cooled to 0° C. and triethylorthoformate (9.6 ml, 58 mmol) was added dropwise. The mixture was allowed to warm up to 20° C. and was stirred for 1 hr before being poured into ice water. This was extracted with dichloromethane and the extracts were washed successively with 10% aqueous ammonia and water and dried over MgSO4. 4-(2-acetoxyethyl)-3,5-dimethylpyrrole-2-carboxaldehyde was purified by silica gel chromatography using (7:3) ethyl acetate:hexane. Yield 45%, m.p. 125–27° C. (water).

Provenance & Evidence