Ammonium Chloride → HCID 25008053, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl (2E,4E,7Z,10Z,13Z,16Z,19Z)-docosa-2,4,7,10,13,16,19-heptaenoate (14) (0.12 g, 0.34 mmol) was dissolved in dry THF (3 mL) and added dropwise to a stirred suspension of LAH (0.013 g, 0.35 mmol) in dry THF (7 mL) at 0° C. The mixture was stirred at 0° C. for 45 minutes, added saturated NH4Cl (5 mL) and filtered through a short pad of celite. The celite was washed with water (10 mL) and heptane (10 mL) and the combined aqueous layer was extracted with heptane (10 mL). The combined organic layer was dried (MgSO4) and purified by flash chromatography (heptane:EtOAc 7:1). This afforded 0.070 g (66%) of the title compound 16 as colourless oil.

Provenance & Evidence