Aluminium lithium hydride → [2-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalen-1-yl]methanol

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Reaction Steps

To a solution of Example 178A (0.3 g, 1 mmol) in tetrahydrofuran (5 mL) was added a 1.0 M solution of lithium aluminum hydride in tetrahydrofuran (1.2 mL, 1.2 mmol) dropwise. The solution was stirred at room temperature for 1 h and then quenched carefully with a saturated solution of NH4Cl (5 mL). The mixture was diluted with water (25 mL) and extracted with ethyl acetate (3× 15 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. Column chromatography on silica (20% ethyl acetate/hexane) afforded product as a colorless oil (0.20 g, 74%). 1H NMR (300 MHz, CDCl3) δ ppm 0.79 (m, 8H), 1.37 (m, 1H), 1.55 (m, 1H), 1.98 (m, 1H), 3.53 (d, J=3.68 Hz, 2H), 3.63 (s, 3H), 3.71 (d, J=10.66 Hz, 1H), 3.95 (m, 1H), 5.09 (t, J=3.68 Hz, 1H), 7.22 (m, 4H); MS m/z 261.0 (M+H)+.

Provenance & Evidence