反应详情

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.

1. customThe reaction mixture was quenched by the careful addition of HCl (5%, aq.) in an equal volume of ice
2. extractionextracted with CH2Cl2
3. dry with materialThe combined organic extracts were dried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated