反应详情

To a stirred solution of 1,2,3,6-tetrahydrobenzylalcohol (1) (1.12 g, 10 mmol) and imidazole (1.36 g, 20 mmol) in DMF (10 mL) was added TBDMSCl (1.81 g, 12 mmol). After 20 hours, the mixture was treated with brine (100 mL) and the product was extracted with hexanes (3×80 mL). The combined organic layers were washed with brine (100 mL), dried over MgSO4 and evaporated in vacuo to give compound (2) (2.26 g, 100%) as colorless liquid. Rf0.29 (hexanes). 1H NMR (CDCl3) δ 5.65-5.64 (m, 2H), 3.48 (d, J=2.3 Hz, 1H), 3.45 (d, J=2.3 Hz, 1H), 2.08-2.00 (m, 3H), 1.82-1.66 (m, 3H), 1.32-1.19 (m, 1H), 0.89 (s, 9H), 0.04 (s, 6H); 13C NMR (CDCl3) δ 127.04, 126.23, 67.95, 36.34, 28.23, 25.97, 25.70, 25.33, 24.78, 18.38, −5.32.

1. extractionthe product was extracted with hexanes (3×80 mL)
2. washThe combined organic layers were washed with brine (100 mL)
3. dry with materialdried over MgSO4
4. customevaporated in vacuo