Dimethylformamide → 1H-Indene-5-carboxaldehyde, 2,3-dihydro-1-(methoxyimino)-

Participants

Reaction Conditions

Reaction Steps

A solution of the product of Step 1 (112 g, 0.46 mol) in tetrahydrofuran (1500 ml) at −60° C. under argon, was treated with n-butyllithium (325 ml of a 1.6M solution in hexanes, 0.52 mol) over 1 hour. After stirring at −60° C. for 1 hour a solution of dimethylformamide (39.7 ml) in tetrahydrofuran (50 ml) was added dropwise over 1 hour. The reaction was stirred at −60° C. for 1 hour before being allowed to warm to room temperature. After 1 hour the reaction was quenched with saturated aqueous sodium hydrogen carbonate solution and extracted into ethyl acetate.

Provenance & Evidence