Sodium borohydride → HCID 86678089, compound

Participants

Reaction Steps

A solution of the keto-alcohol (6Z,9Z,29Z,32Z)-20-((8Z,11Z)-heptadeca-8,11-dien-1-yl)-21-hydroxyoctatriaconta-6,9,29,32-tetraen-19-one (10) (920 mg, 1.16 mmol) in CH3OH (5 mL) and isopropanol (12 mL) was treated with NaBH4 (88 mg, 2.3 mmol). After stirring (1 h) a second portion of NaBH4 (88 mg, 23 mmol) was added and the mixture stirred (3 h). The reaction mixture was carefully quenched by the addition of cold HCl (5% aq.), extracted with CH2Cl2, washed with brine, dried (Na2SO4), filtered and concentrated. The crude material was subjected to chromatography (1%→10% EtOAc-hexanes) to yield (6Z,9Z,29Z,32Z)-19-((8Z,11Z)-heptadeca-8,11-dien-1-yl)octatriaconta-6,9,29,32-tetraene-18,20-diol (11) (832 mg, 90%) as a colorless oil. Rf 0.23 (10% EtOAc-hexanes), FW 793.39, C55H100O2.

Provenance & Evidence