7-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one → 1-Methylene-7-methoxy-1,2,3,4-tetrahydronaphthalene

Participants

Reaction Steps

To a solution of 7-methoxy-1-tetralone H4.1 (26.9 g, 153 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) and triphenylmethylphosphonium bromide (65.4 g, 183 mmol) in THF (550 mL) was added potassium tert-butoxide (1.0 M solution in THF)(183 mL, 183 mmol) via addition funnel over 1 hour. The resulting mixture was stirred at room temperature for 60 minutes after addition. The reaction was then concentrated and resuspended in hexanes (250 mL). The mixture was passed through a silica gel plug (25 g silica) and rinsed with 250 mL of hexanes. Removal of solvent gave H4.2 (24.5 g, 92% yield). MS ESI (pos.) M/E: 175 (M+H).

Provenance & Evidence