Dimethylformamide → HCID 10800448, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of magnesium (228 mg) and iodine (3 mg) in tetrahydrofuran (3 ml) is heated at 60° C. under argon atmosphere, and thereto is added dropwise with stirring a solution of 6-bromo-1-tetrahydropyranyloxyindane (2.60 g) in tetrahydrofuran (5 ml). After addition, the mixture is stirred at 70° C. for one hour. To the mixture is added dropwise a solution of dimethylformamide (959 mg) in tetrahydrofuran (2 ml) under ice-cooling, and the mixture is stirred under ice-cooling for one hour. The reaction solution is poured into a mixture of ice-acetic acid, and extracted with ethyl acetate. The extract is washed with water, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; hexane/ethyl acetate) to give 1-tetrahydropyranyloxyindane-6-carbaldehyde (1081 mg).

Provenance & Evidence