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

HRID 1197185Notes

Reaction equation

[Na].[H-].COCCO[Al+2].[H-].[OH:10][CH:11]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[C:12]#[C:13][C:14]1[N:19]=[C:18]([CH2:20][C:21]2[O:26][C:25](=[O:27])[CH:24]=[CH:23][CH:22]=2)[CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[OH:10][CH:11]([CH2:28][CH:29]=[CH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:12][CH2:13][C:14]1[N:19]=[C:18]([CH2:20][CH:21]([OH:26])[CH2:22][CH2:23][CH2:24][CH2:25][OH:27])[CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

customquenched with 0.100 ml water
stirringstirred vigorously overnight with 10 ml 0.5M sodium potassium tartrate
extractionThe mixture is extracted with 4×10 ml ethyl acetate
dry with materialThe combined organics are dried over magnesium sulfate
concentrationconcentrated in vacuo to a pale oil

Sources & evidence

ORD record: ord-2eaaabbcc9ec4cb081921e2a9b615802
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05116981

Reaction notes

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