Water → Arachidonyl alcohol

Temperature

0 °C

To a suspension of LiAlH4 (0.499 g, 13.14 mmol) in dry THF (50 mL) was added arachidonic acid (1.00 g, 3.28 g) in dry THF (40 mL) at 0° C. (ice-bath) under argon and the reaction mixture was stirred for 1 h at 0° C. and then for 1 h at room temperature. After a slow addition of water (0.2 mL), the white gelatinious precipitate was dissolved by adding 10% aq NaOH (0.2 mL) and water (0.6 mL) and the mixture was allowed to stir for 1 h. The mixture was then dried over MgSO4, and filtered and the filtrate was concentrated under reduced pressure to furnish a crude, which was purified over silica-gel column chromatography using 20% ethyl acetate/hexane to give the product as a clear oil (0.945 g, 99%). 1H NMR (CDCl3): δ5.37 (m, 8H), 3.64 (t, 2H, J=6.4 Hz), 2.81 (m, 6H), 2.09 (m, 4H), 1.61 (m, 2H), 1.50-1.30 (m, 8H), 1.04 (t, 3H, J=6.8 Hz). m/z (APCI) 291.43 (M++1).

1. waitfor 1 h at room temperature
2. dissolutionthe white gelatinious precipitate was dissolved
3. stirringto stir for 1 h
4. dry with materialThe mixture was then dried over MgSO4
5. filtrationfiltered
6. concentrationthe filtrate was concentrated under reduced pressure
7. customto furnish a crude, which
8. customwas purified over silica-gel column chromatography

ORD record

ord-74970ca136ed4b73ad22ad6d9f2b5705

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563760B2