Sodium borohydride → HCID 86678082, compound

Participants

Reaction Steps

A cooled (0° C.) solution of (11Z,14Z)-methyl 3-oxoicosa-11,14-dienoate (2) (3.5 g, 10.4 mmol) in dry methanol (75 mL) was treated with NaBH4 (787 mg, 20.8 mmol) and stirred (20 min). The reaction mixture was quenched by the careful addition of HCl (5%, aq.) in an equal volume of ice and extracted with CH2Cl2. The combined organic extracts were dried (Na2SO4), filtered, concentrated and the residue was subjected to flash chromatography (2%→10% EtOAc-hexanes) to yield (11Z,14Z)-methyl 3-hydroxyicosa-11,14-dienoate (3) (2.51 g, 71%) as a pale yellow oil. Rf 0.37 (30% EtOAc-hexanes). FW 338.51, C21H38O3.

Provenance & Evidence