反应详情

2.7 g trans-2-(3-methylsulfonyl-4-n-propoxy-5-benzyloxyphenyl)-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran dissolved in 15 mL THF was cooled to 78° and treated with 5.3 mL of 1.6M n-BuLi. After about 5 minutes of stirring, to the resulting dark solution, 1.0 mL of acetic anhydride was added. The yellow reaction mixture was allowed to warm up to room temperature and treated with 3-4 g of solid ammonium chloride, water and ether. The ether layer was separated, dried over NaSO4, evaporated and chromatographed over silica (20% ethyl acetate in hexane) to yield the title compound after crystallization from ether: NMR (200 MHz, CDCl3) δ0.98 (t, CH2CH2CH3), 1.83 (m, CH2CH2CH3), 1.9-2.6 (m, 3-CH2 & 4-CH2), 2.38 (s, CH3C(O)CH2), 3.86 (s, OCH3), 3.88 (s, 2 OCH3), 4.18 (t, OCH2CH2CH3), 4.48 (s, CH3C(O)CH2), 5.18 (s, OCH2Ar), 5.06-5.28 (m, 2-CH & 5-CH), 6.61 (s, 5-ArH), 7.32-7.54 (m, ArH).

1. temperaturewas cooled to 78°
2. additionwas added
3. customThe ether layer was separated
4. dry with materialdried over NaSO4
5. customevaporated
6. customchromatographed over silica (20% ethyl acetate in hexane)