Ethyl acetate hexane → (3-Hexyl-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)-methanol

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Reaction Steps

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).

Provenance & Evidence