Ammonium Chloride → Dec-4-en-1-ol

Participants

Reaction Steps

Sodium borohydride (0.60 g, 3.8 mmol) was added in portions to a stirred solution of trans-dec-4-enal (1.54 g, 10.0 mmol) in methanol (50 mL). The reaction was stirred at room temperature for 30 min followed by the addition of saturated NH4Cl. Methanol was evaporated and water was added to the residue. The mixture was extracted with ether and the combined organic layers were washed with water and dried. Evaporation of the solvent gave trans-dec-4-en-1-ol (1.52 g, 97%) as a pale yellow oil, which was used in the next step without further purification: 1H NMR (300 MHz, CDCl3) δ 5.39 (2H, m), 3.60 (2H, t, J=6.6 Hz), 2.02 (5H, m), 1.56 (2H, m), 1.23 (6H, m), 0.84 (3H, t, J=6.9 Hz); 13C NMR (75 MHz, CDCl3) δ 131.31, 129.44, 62.66, 32.80, 32.70, 31.67, 29.51, 29.18, 22.82, 14.36.

Provenance & Evidence