反应详情

A solution of 4.14 g of 3-hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-aldehyde (from Example 4.1) in 20 ml of THF was cooled to 0° C. and treated with 13.8 ml of borane-THF complex sol. 1M in THF (3 H eq.). The mixture was stirred at room temperature for 90 min., then cooled back at 0° C. and quenched carefully by the addition of 30 ml of hydrochloric acid 3N. The mixture was stirred at room temperature for 30 min., then was extracted with 3 portions of 100 ml ether. The combined extracts were washed with water (100 ml) and a saturated aqueous sodium chloride solution (100 ml). The organic phase was dried over MgSO4, filtered and concentrated in vacuo, giving a pale yellow oil. Flash chromatography (SiO2, 10% ethyl acetate/hexane) afforded 3.80 g of the title compound as a colourless oil. 1 H NMR (CDCl3): 7.27 (s, 1H), 7.11 (s, 1H), 4.67 (d, J=5.7 Hz, 2H), 2.59 (t, J=8.3 Hz, 2H), 1.67 (s, 4H), 1.50-1.65 (m, 2H), 1.20-1.45 (m,6H), 1.28 (s, 6H), 1.27 (s, 6H), 0.89 (t, J=6.6 Hz, 3H).

1. temperaturecooled back at 0° C.
2. customquenched carefully by the addition of 30 ml of hydrochloric acid 3N
3. stirringThe mixture was stirred at room temperature for 30 min.
4. extractionwas extracted with 3 portions of 100 ml ether
5. washThe combined extracts were washed with water (100 ml)
6. dry with materialThe organic phase was dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customgiving a pale yellow oil