Tetrahydrofuran → HCID 18666732, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (-)-(R)-6-methyl-9-phenyl-(E)-4-nonenoic acid ethyl ester, prepared by the procedure described in J. Org. Chem., 59(8), 2253 (1994), (1.0 g, 3.8 mmol) and 7.9 mL of anhydrous THF was added dropwise to a 0° C. suspension of LAH (0.03 g, 7.9 mmol) and 7.9 mL of anhydrous THF. The reaction mixture was stirred for 2 hours at 0° C. and for 1 hour at room temperature. After cooling again to 0° C., 1.2 mL of MeOH was added slowly. The mixture was stirred for 0.25 hours at room temperature, then concentrated in vacuo. Saturated aqueous Rochelle's salt was added, and the mixture was extracted with isopropyl acetate. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound (0.84 g) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 0.095 (d, 3H), 1.21-1.38 (m, 3H), 1.51-1.70 (m, 4H), 2.02-2.15 (m, 3H), 2.58 (t, 2H), 3.65 (q, 2H), 5.23-5.45 (m, 2H), 7.18 (m, 3H), 7.28 (m, 2H). MS (DCl/NH3) m/e 250 (M+NH4)+.

Provenance & Evidence