Borane → HCID 53675379, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of THF (2.5 ml), methanol (5 ml) and triethylborane (1M in THF) (12 ml) was stirred at a temperature from -50 to -60° C. for one hour in an argon atmosphere. A solution of 1-methyl 6-ethyl 2-hydroxy-4-oxoadipate (2.2 g, 10 mmol) in THF (2.5 ml) was dropwise added to the above borane solution at -60° C. After stirring at -78° C. for 60 minutes, sodium borohydride (378 mg, 10 mmol) was added in one portion, followed by stirring at -78° C. for 2 hours. After dropwise adding acetic acid (3 ml) to the reaction solution at -78° C., the solution was stirred for 15 minutes. After adding water (5 ml), THF was evaporated off. After adding ethanol (10 ml) and a 10 % hydrogen peroxide (1.5 ml) at room temperature, 1 N hydrochloric acid was added to adjust pH to 7, followed by stirring for one hour. After adding a 5 % aqueous solution of sodium sulfite (15 ml) and stirring the mixture at room temperature for 40 minutes, the mixture was extracted with methylene chloride and organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:acetone=5:1) to give pure 1-methyl 6-ethyl 2,4-dihydroxyadipate (1.52 g, 6.9 mmol). Yield, 69 %.

Provenance & Evidence