反应详情

温度

0 °C

To a solution of ester 24 (1.35 g, 4.41 mmol) in toluene (60 mL) under N2 at −78° C. was added DIBAL-H (8.8 mL of a 1M solution in toluene, 8.8 mmol) dropwise. The reaction was then warmed to 0° C. and stirred for 30 minutes, then quenched with 30 mL of saturated Rochelle's salt and the mixture stirred overnight. The bilayer was transferred to a separatory funnel and the organic layer washed with H2O and brine and dried (MgSO4). After filtration the organic layer was concentrated under reduced pressure to provide a yellow oil which was purified by silica gel chromatography eluting with 1:1 hexanes:EtOAc, then EtOAc. The allylic alcohol 25 (900 mg, 73%) was isolated as a pale yellow oil. 1H NMR (CDCl3; 400 MHz): δ: 8.72 (s, 1 H), 8.27 (s, 1H), 7.66 (m, 2H), 7.62 (m, 1H), 7.47 (m, 3H), 7.34 (m, 1H), 7.24 (m, 2H), 6.82 (dd, 1h), 6.56 (m, 1H), 4.41 (dd, 1H).

1. customquenched with 30 mL of saturated Rochelle's salt
2. stirringthe mixture stirred overnight
3. customThe bilayer was transferred to a separatory funnel
4. washthe organic layer washed with H2O and brine
5. dry with materialdried (MgSO4)
6. filtrationAfter filtration the organic layer
7. concentrationwas concentrated under reduced pressure
8. customto provide a yellow oil which
9. customwas purified by silica gel chromatography
10. washeluting with 1:1 hexanes