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

HRID 1197182Notes

Reaction equation

[Na].[H-].COCCO[Al+2].[H-].C[O:11][C:12](=O)[CH2:13][CH2:14][CH2:15][CH:16]1[O:28][CH:17]1[C:18]1[NH:19][C:20](=[CH:24][CH2:25][CH2:26][OH:27])[CH:21]=[CH:22][CH:23]=1>C1(C)C=CC=CC=1>[OH:27][CH2:26][CH:25]=[CH:24][C:20]1[N:19]=[C:18]([CH:17]2[O:28][CH:16]2[CH2:15][CH2:14][CH2:13][CH2:12][OH:11])[CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

customquenched with the careful addition of 5 ml 0.5M sodium potassium tartrate
stirringstirred vigorously for 1.5 hours
temperaturewhile warming to room temperature
additionThe mixture is poured into 15 ml saturated sodium chloride
extractionextracted with r×10 ml ethyl acetate
dry with materialThe combined organics are dried over magnesium sulfate
concentrationconcentrated in vacuo to an amber oil (64 mg)

Sources & evidence

ORD record: ord-62453084ca544da1a6d76fb9c87ead35
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05116981

Reaction notes

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