Sodium → 6-[6-(3-Hydroxy-5-undecenyl)-2-pyridinyl]-1,5-hexanediol

Participants

Reaction Conditions

Reaction Steps

Sodium (bis) 2-methoxyethoxy-aluminum hydride (24 ml, 82 mmol) is dissolved in 150 ml dry toluene in a flame-dried, 500 ml 3-neck round bottom flask under nitrogen at 0° C. 6-[1-[6-(3-hydroxyl-5-undecen-1-ynyl)pyridinyl]methyl]pyran-2-one (5.83 g, 14 mmole), in 4×10 ml dry toluene, is added slowly dropwise to the reaction mixture at 0° C. The reaction is stirred 20 minutes at 0° C. and then an additional 7 hours at room temperature. The reaction is quenched by the careful addition of 3 ml water. The mixture is stirred vigorously overnight with 1×160 ml 0.5M sodium potassium tartrate. The mixture is extracted with 3×100 ml ethyl acetate. The combined organics are washed with 1×100 ml saturated sodium chloride and dried over magnesium sulfate. The organics are concentrated in vacuo to a crude amber oil (35 g).

Provenance & Evidence