反应详情

TiCl4 (2.10 mL, 19.0 mmol) was added dropwise to a suspension of zinc powder (2.51 g, 38.4 mmol) in anhydrous THF (60 mL) at RT. After refluxing for 1 h, a mixture of 76 (1.40 g, 4.74 mmol) and cyclohexanone (1.40 g, 14.3 mmol) dissolved in THF (20 mL) was added dropwise. Refluxing was continued for 30 min. The reaction mixture was cooled to RT and filtered through Celite. Water (250 mL) was added and the mixture was extracted with Et2O (3×100 mL). The combined ethereal extracts were washed with water (200 mL), brine (200 mL), and dried over MgSO4. Concentration followed by flash chromatography (20:1 to 5:1 hexanes:EtOAc) afforded 1.23 g (72%) of 77 as a white solid. 1H NMR (400 MHz, CDCl3): δ 1.58 (br s, 6H), 2.05 (m, 2H), 2.25 (m, 2H), 4.68 (br s, 1H), 6.73 (d, J=8.6 Hz, 2H), 6.94-7.00 (m, 3H), 7.19 (d, J=7.9 Hz, 2H).

1. temperatureAfter refluxing for 1 h
2. additionwas added dropwise
3. temperatureRefluxing
4. filtrationfiltered through Celite
5. additionWater (250 mL) was added
6. extractionthe mixture was extracted with Et2O (3×100 mL)
7. washThe combined ethereal extracts were washed with water (200 mL), brine (200 mL)
8. dry with materialdried over MgSO4
9. concentrationConcentration