Hydrochloric Acid → HCID 22633673, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 7-bromo-4,4-dimethyl-1-oxo-1,2,3,4-tetrahydronaphthalene (2.0 g, 7.9 mmol) in benzene (34 ml) was added to a cold (0° C.) suspension of sodium hydride (60% in oil, 2.28 g, 57 mmol) and sodium methoxide (24 mgs) in benzene (34 ml). Ethyl formate (2.74 ml, 33.9 mmol) was then added dropwise and the mixture was stirred at 0° C. for 2 hours and then at room temperature for 3 hours. Wet methanol was then added and the aqueous phase was acidified with 4M hydrochloric acid and extracted with ethyl acetate (3×). The combined organic phases were washed with 2M sodium carbonate and the sodium carbonate phases were combined, acidified and reextracted with ethyl acetate. The combined organic phases were dried over anhydrous magnesium sulfate, concentrated and purified by silica gel chromatography (ethyl acetate/hexane 10:90) to give the title material (2.1 g, 95%).

Provenance & Evidence