反应详情

To a stirred solution of LiAlH4 (1.7 g, 45 mmol) in dry ether (60 ml) a solution of acetate 2 (3.2 g, 15 mmol) in ether (20 ml) was added dropwise while cooling with ice water. Stirring was continued for 1 h and the residual LiAlH4 was destroyed with water. The aqueous layer was separated and twice extracted with ether (30 ml). The combined extracts were washed with brine (50 ml) and dried over MgSO4. After concentration in vacuo an oily residue was purified by Kugelrohr short path distillation (150-170° C., 11 mm Hg) to give 3 (2.3 g, 89%) as an oil. 1H NMR (CDCl3, TMS): 0.92 (6H, s, 3,5-CH3); 1.10 (1H, br s, OH); 1.28 (2H, s, 4-CH2); 1.87 and 1.94 (total 4H, both s, 2,6-CH2); 4.16 (2H, d, 7 Hz, CH2O) and 5.50 ppm (1H, t, 7 Hz, ═C—H).

1. customthe residual LiAlH4 was destroyed with water
2. customThe aqueous layer was separated
3. extractiontwice extracted with ether (30 ml)
4. washThe combined extracts were washed with brine (50 ml)
5. dry with materialdried over MgSO4
6. concentrationAfter concentration in vacuo an oily residue
7. distillationwas purified by Kugelrohr short path distillation (150-170° C., 11 mm Hg)