Ammonium Chloride → Dec-4-en-1-ol

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.

1. customMethanol was evaporated
2. additionwater was added to the residue
3. extractionThe mixture was extracted with ether
4. washthe combined organic layers were washed with water
5. customdried
6. customEvaporation of the solvent

ORD record

ord-3045a0f05464439483f978fcd3de00c1

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07091357B2