反应详情

To a mixture of 3-phenylpropionaldehyde (1.06 mL, 8 mmol, 1 eq) and activated zinc (628 mg, 9.6 mmol, 1.2 eq) in THF (3.2 mL) at 0° C. was added one drop of allyl bromide. After the reaction was initiated, the remaining allyl bromide (total 0.831 mL, 9.6 mmol, 1.2 eq) was added slowly. The contents were stirred overnight at room temperature. After 20 hours the reaction was quenched with saturated aq. NH4Cl solution (15 mL), extracted with ether (3×20 mL) and the combined organic phases washed with brine (15 mL). The organic layer was dried over MgSO4 and the solvent was removed under reduced pressure to give crude 1-phenyl-hex-5-en-3-ol as a yellow oil. Column chromatography (hexane:ether, 85:15, 80:20, 75:25) gave a colourless oil, (966 mg, 69% yield). 1H NMR (400 MHz, CDCl3) δ 1.80-1.85 (m, 3H, CCH2CH2, +COH), 2.19-2.26 (m, 1H, CHOHCH2CH), 2.33-2.39 (m, 1H, CHOHCH2CH) 2.69-2.76 (m, 1H, PhCH2CH2), 2.82-2.89 (m, 1H, PhCH2CH2), 3.69-3.74 (m, 1H, CHOH), 5.16-5.19 (s, 1H, CHCH2 (cisH)), 5.19-5.20 (d, 1H, CHCH2 (trans H)), 7.21-7.26 (m, 3H, PhCH2), 7.30-7.34 (m, 2H, PhCH2); 13C NMR (100 MHz, CDCl3) δ 32.0 (PhCH2CH2), 38.4 (CH2CH2CH), 42.0 (CHOHCH2CH), 69.9 (CHOH), 118.1 (CHCH2), 125.7 (Ph), 128.4 (Ph), 128.5 (Ph), 134.6 (CHCH2), 142.0 (Ph); IR (v, cm−1) 3385 (OH), 3027 (Ar), 2932 (CH2), 1641 (CH═CH2), 1496 (Ph), 916 (CH═CH2); MS (GCT, CI+) m/z 194.2 [M+NH4]+ HRMS required for C12H20NO: 194.1545, found 194.1543.

1. customAfter 20 hours the reaction was quenched with saturated aq. NH4Cl solution (15 mL)
2. extractionextracted with ether (3×20 mL)
3. washthe combined organic phases washed with brine (15 mL)
4. dry with materialThe organic layer was dried over MgSO4
5. customthe solvent was removed under reduced pressure
6. customto give crude 1-phenyl-hex-5-en-3-ol as a yellow oil