反应详情

To a solution of 3,4-dimethoxythiophenol (8.25 mL, 57.6 mmol) in anhydrous THF (100 mL) at 0° C., is added n-BuLi (2.5 M in hexane, 0.77 mL, 1.92 mmol) and the solution is stirred for 15 minutes under a nitrogen atmosphere. t-butyl 7-phenyl-2-heptenoate (10 g, 38.4 mmol) in THF (100 mL) is added dropwise and the mixture is allowed to warm to room temperature and stir overnight. TLC analysis indicated complete reaction. The reaction mixture is diluted with water (300 mL) and extracted with ether (3×250 mL). Combined organic extracts are washed successively with sat. Na2CO3 solution (4×200 mL), water (200 mL) and brine (200 mL) then dried over MgSO4 and concentrated to afford a pale yellow oil which is chromatographed on silica gel (pet-ether/EtOAc, 9:1) to afford 14.9 g of (±)-t-butyl-3-(3,4-dimethoxyphenyl)sulfanyl-7-phenylheptanoate (90%) as a colorless oil. TLC analysis [pet-ether/EtOAc, 9:1, Rf (heptenoate)=0.80, Rf (heptanoate)=0.50]. 1H NMR (300 MHz, CDCl3) δ 1.44 (s, 9H), 1.48-1.68 (m, 6H), 2.42 (dABq, 2H), 2.60 (t, 2H), 3.28 (t, 1H), 3.85 (d, 6H), 6.75 (d, 1H), 7.0 (dd, 2H), 7.15 (d, 3H), 7.25 (t, 2H) ppm. Mass spectrum (FAB) m/z 447 (M+H)+.

1. stirringstir overnight
2. customreaction
3. extractionextracted with ether (3×250 mL)
4. washCombined organic extracts are washed successively with sat. Na2CO3 solution (4×200 mL), water (200 mL) and brine (200 mL)
5. dry with materialthen dried over MgSO4
6. concentrationconcentrated
7. customto afford a pale yellow oil which
8. customis chromatographed on silica gel (pet-ether/EtOAc, 9:1)