Triethylamine → 1-(4-Methoxybenzyl)-5-oxopyrrolidine-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

In a three necked flask, under argon, a solution 4-hydroxymethyl-1-(4-methoxy-benzyl)-pyrrolidin-2-one a2 (4.3 g, 0.018 mol) and Et3N (8.9 ml) in CH2Cl2 (25 ml) cooled down to −10° C. Pyridine-SO3 (10.1 g, 0.064 mol, 3.5 eq) is added by portions and the temperature raised up to 1° C. After 3 h at −10° C., the reaction is quenched with water (100 ml) and extracted with CH2Cl2 (3 times). The organic phase is washed with successively a 1M solution of KHSO4, water, brine, dried over MgSO4, filtered and evaporated in vacuo to give the crude aldehyde a3 (3.2 g, 87%). It is dried several times by azeotropic distillation with toluene and used as such in the next step.

Provenance & Evidence