Ethyl 1,4-dimethyl-3-(2'-nitrophenyl)-2-pyrrolecarboxylate → 1,4-Dimethyl-2-hydroxymethyl-(2'-nitrophenyl) pyrrole

Participants

Reaction Conditions

Reaction Steps

200 mg (7) are dissolved in 30 ml of anhydrous methylene chloride and the solution is cooled to -78° C. in a bath (acetone/dry ice). 2.8 ml (4 equivalents) of 1M dibal in toluene are added dropwise. Stirring is maintained for 2 hours at -78° C., the flask is then removed from the cooling medium and 50 ml of aqueous (10%) sodium carbonate solution are introduced. A substantial emulsion appears, and is removed by filtration on celite. The clear organic phase collected is washed with water saturated with sodium chloride and dried over sodium sulfate. The alcohol (12) is purified on a silica column (120 mg ; Yld 71%).

Provenance & Evidence