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

Participants

Reaction Conditions

Reaction Steps

Sodium (bis) 2-methoxyethoxy-aluminum hydride (0.52 ml, 1.78 mmole) is dissolved in 2 ml dry toluene in an oven-dried 50 ml 2-neck round bottom flask under nitrogen at 0° C. 6-[1-[6-(3-Hydroxy-undec-1ynyl)-pyridine-2yl]-methyl-]pyran-2-one (160 mg, 0.445 mmole), in 2×1 ml dry toluene, is added slowly dropwise to the reaction mixture at 0° C. The mixture is stirred 7 hours at 0° C., quenched with 0.100 ml water, and stirred vigorously overnight with 10 ml 0.5M sodium potassium tartrate. The mixture is extracted with 4×10 ml ethyl acetate. The combined organics are dried over magnesium sulfate and concentrated in vacuo to a pale oil.

Provenance & Evidence