反应详情

To a solution of 224 (1.25 g, 6 mmol) in DCM (50 ml) was added imidazole (1.73 g, 25.4 mmol) and triisopropylsilyl chloride (2.71 ml, 12.7 mmol). The reaction mixture was stirred at rt for 22 h. Water (30 ml) and Chloroform (30 ml) were added. The layers separated and the aqueous layer extracted with chloroform (3×30 ml). The combined organic layers were washed with brine (30 ml), dried (MgSO4) and concentrated in vacuo. Purification by column chromatography eluting with EtOAc:MeOH:TEA; 10:1:01 afforded the title compound (1.78 g, 81%) as colourless oil. 1H NMR (270 MHz; CDCl3) 1.06 (18H, d, J=6.7 Hz, 6×CH3CH), 1.14 (6H, s, 2×CH3), 1.14-1.28 (3H, m, 3×CH), 2.51 (2H, s, CH2), 3.74 (3H, s, OCH3), 3.89 (2H, s, CH2), 6.46 (1H, s, CH), 6.51 (1H, s, CH). 13C NMR (67.5 MHz; CDCl3) 12.95 (CH3), 18.03 (CH3), 27.76 (CH), 41.17 (CH2), 43.97 (CH2), 48.78 (C(CH3)2), 55.56 (OCH3), 112.96 (CH), 117.39 (CH), 126.24 (C), 126.92 (C), 143.58 (C), 149.34 (C). LC/MS (ES+) tr=2.65 min, m/z 364.36 (M++H).

1. customThe layers separated
2. extractionthe aqueous layer extracted with chloroform (3×30 ml)
3. washThe combined organic layers were washed with brine (30 ml)
4. dry with materialdried (MgSO4)
5. concentrationconcentrated in vacuo
6. customPurification by column chromatography
7. washeluting with EtOAc