Hydrochloric Acid → 2-Acetyl-8,8-dimethyl-5,6,7,8-tetrahydronaphthalene

Participants

Reaction Conditions

Reaction Steps

A solution of 7-bromo-1,1-dimethyl-1,2,3,4-tetrahydro-naphthalene (Compound 15, 1.20 g, 5.94 mmol) in 20 ml of THF was first degassed by bubbling with argon for 30 min. Tributyl(1-ethoxyvinyl)tin (4.29 g, 11.88 mmol) and PdCl2(PPh3)2 (422 mg, 0.60 mmol) were added. After stirring at 80° C. for 18 h, the mixture was cooled to room temperature and 3 mL of 10 % HCl was added. The mixture was then stirred for another 30 min, then extracted with ethyl acetate (3×10 mL). The combined organic layer was washed with brine (1×10 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (80:20 hexane/ethyl acetate) afforded the title compound (669 mg, 56% yield) as a colorless oil:

Provenance & Evidence