反应详情

To a solution of 7-methoxy-3,4-dihydronaphthalen-1(2H)-one 46.1 (10.0 g, 56.7 mmol, Aldrich) and triethyl phosphonoacetate (13.6 mL, 68.1 mmol) in THF (250 mL) was added potassium tert-butoxide (1.0M solution in THF (68.1 mL, 68.1 mmol)) via addition funnel over 15 minutes. The resulting mixture was stirred at room temperature for 16 hours (LC-MS showed no difference between 15 minutes and 16 hours) after addition. The mixture was concentrated and re-suspended in hexanes (250 mL). The mixture was passed through a silica gel plug (50 g silica) and rinsed with 1 L of hexanes. The resulting mixture was concentrated to give two pure products (535 mg and 267 mg). Both products were dissolved in EtOH and stirred with Pd/C under H2 for 16 hours. LC-MS showed that both gave the same desired product. The mixture was combined, filtered, and concentrated to give 46.2 (0.77 g, 5.5% yield). MS ESI (pos.) M/E: 249 (M+H).

1. additionvia addition funnel over 15 minutes
2. customno difference between 15 minutes and 16 hours
3. additionafter addition
4. concentrationThe mixture was concentrated
5. washrinsed with 1 L of hexanes
6. concentrationThe resulting mixture was concentrated
7. customto give two pure products (535 mg and 267 mg)