Aluminium lithium hydride → HCID 22117814, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1.5 g of N-methoxy-N-methyl-4-chloro-3-(1H-pyrrol-1-yl)benzamide in 30 ml of anhydrous tetrahydrofuran was added drop-wise over a period of 30 minutes to a solution, pre-cooled to 0-5° C., of 237 mg of lithium aluminium hydride (98%) in 30 ml of anhydrous tetrahydrofuran. The mixture was stirred at 0-5° C. for a further 45 minutes and ther reaction was then quenched by the adition of 25 ml of saturated aqueous ammonium chloride solution and 25 ml of 50% aqueous hydrochloric acid. The mixture was then extracted with three 100 ml portions of diethyl ether and the combined extracts were dried over anhydrous magnesium sulphate. The solvents were removed under reduced pressure and the residue was purified by column chromatography on silica gel using hexane/ethyl acetate (90:10) as the eluent to give 0.84 g of 4-chloro-3-(1H-pyrrol-1-yl)benzaldehyde as a yellow oil; nmr (CDCl3,250 Mhz) dH 10.00 (CHO).

Provenance & Evidence