Aluminium lithium hydride → HCID 25010673, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl (2E,7Z,10Z,13Z,16Z,19Z)-3-methyl-docosa-2,7,10,13,16,19-hexaenoate (2E:2Z=9:1), (0.40 g, 1.08 mmol) was dissolved in dry THF (5 mL) and added dropwise to a cold suspension of LAH (0.045 g, 1.19 mmol) in dry THF (10 mL). The mixture was stirred at 0° C. under inert atmosphere for 30 minutes, followed by 18 hours at ambient temperature. The reaction was quenched by addition of 10% NH4Cl (20 mL) and the mixture was extracted twice with heptane (30 mL). The combined organic extracts were washed with brine (20 mL) and dried (Na2SO4). Purification by flash chromatography (heptane:EtOAc 4:1) afforded 0.16 g (45%) of 3-methyl-(2E,7Z,10Z,13Z,16Z,19Z)-docosa-2,7,10,13,16,19-hexaen-1-ol as a colourless oil.

Provenance & Evidence