Sodium → 3-[6-(3-Hydroxy-1-propenyl)-2-pyridinyl]-oxiranebutanol

Participants

Reaction Conditions

Reaction Steps

Sodium (bis) 2-methoxyethoxy-aluminum hydride (0.31 ml, 1.05 mmole) is dissolved in 1 ml toluene in an oven-dried 10 ml 2-neck round bottom flask under nitrogen at 0° C. Methyl-5,6-epoxy-6-[6-(3-hydroxy-propyl-1yl)pyridine-2yl]-hexanoate (72 mg, 0.263 mmole), in 3×0.3 ml toluene, is added dropwise to the reaction mixture at 0° C. The reaction mixture is stirred 4 hours at 0° C., quenched with the careful addition of 5 ml 0.5M sodium potassium tartrate, and stirred vigorously for 1.5 hours while warming to room temperature. The mixture is poured into 15 ml saturated sodium chloride and extracted with r×10 ml ethyl acetate. The combined organics are dried over magnesium sulfate and concentrated in vacuo to an amber oil (64 mg).

Provenance & Evidence