反应详情

2-Hydroxymethylene-6-methoxy-1-tetralone (2) (4.81 g, 0.024 mole) and borane:t-butylamine complex (10.25 g, 0.12 mole) were dissolved in about 250 mL of methylene chloride and the solution was cooled to about -78°. Boron trifluoride etherate (14.5 mL, 0.12 mole) was added dropwise and the mixture was stirred for about 1 hour then warmed to about 23° and stirred for an additional 2 hours. The reaction mixture was quenched with about 1N HCl and extracted with methylene chloride. The methylene chloride extracts were dried (MgSO4) and concentrated in vacuo. The crude oil was purified by flash chromatography [gradient 3:1 to 1:2 Hexanes:Ether] to yield the title compound as a light yellow oil (3.41 g, 0.018 mole, 75% yield): IR (Film) 3362, 2996, 2918, 1610, 1504, 1464, 1264, 1234, 1040 cm-1 ; 1H NMR (CDCl3) δ1.40 (m, 1H), 1.47 (s, 1H), 1.95 (m, 2H), 1.39,1.45 (d of d, J=10.6,16.1 Hz, 1H), 2.81 (m, 2H), 3.62 (d, J=6.3 HZ, 2H), 3.77 (s, 3H), 6.62 (d, J=2.6 Hz, 1H), 6.68 (d of d, J=8.4,2.6 Hz, 1H), 6.98 (d, J=8.4 Hz, 1H); MS m/e 193 (MH+).

1. temperaturethe solution was cooled to about -78°
2. temperaturethen warmed to about 23°
3. stirringstirred for an additional 2 hours
4. customThe reaction mixture was quenched with about 1N HCl
5. extractionextracted with methylene chloride
6. dry with materialThe methylene chloride extracts were dried (MgSO4)
7. concentrationconcentrated in vacuo
8. customThe crude oil was purified by flash chromatography [gradient 3:1 to 1:2 Hexanes:Ether]