Aluminium lithium hydride → HCID 21866519, compound

Participants

Reaction Steps

2.44 g (64 mmol) of lithium aluminum hydride were added portionwise at 0° C. to a solution of 25.1 g (129 mmol) of ethyl 3-cyano-4-methylthiophene-5-carboxylate in 400 ml of tetrahydrofuran. The mixture was stirred for 5 hours at room temperature, excess reducing agent was destroyed by adding 0.5 N hydrochloric acid, and the reaction mixture was concentrated under a water pump vacuum, diluted with water and extracted three times with ethyl acetate. The combined organic phases were then washed in each case once with 0.5 N hydrochloric acid and saturated sodium chloride solution. The organic phase was dried over magnesium sulfate, the desiccant was filtered off, and the solvent was distilled off under a water pump vacuum at room temperature. The residue was purified by column chromatography (eluant dichloromethane/methanol 95:5), and 16.1 g (83%) of the desired compound were obtained as a slightly yellow oil.

Provenance & Evidence