N-Methoxy-N-methylhexanamide → HCID 22640671, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 7-bromo-4,4-dimethyl-chroman (1.0 g, 4.15 mmole) in 20 mL of THF at −78° C., was treated with 1.91 mL of 2.5M butyllithium. After 30 minutes at −78° C. a solution of hexanoic acid methoxy-methyl-amide (0.726 g, 4.56 mmole) in 5 mL of THF was added. The reaction mixture was stirred at −78° C. for 30 minutes, warmed to room temperature, quenched by the addition of 25 mL saturated aqueous ammonium chloride solution and extracted with three 25 mL portions of ether. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The product was purified by flash chromatography (SiO2, 5% ethyl acetate in hexanes) to yield 0.516 g of 1-(4,4-dimethyl-chroman-7-yl)-hexan-1-one as a colorless oil.

Provenance & Evidence