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

HRID 1197186Notes

Reaction equation

[Na].[H-].COCCO[Al+2].[H-].[OH:10][CH:11]([CH2:28][CH:29]=[CH: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 (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).

Workup

customan additional 7 hours
customat room temperature
customThe reaction is quenched by the careful addition of 3 ml water
stirringThe mixture is stirred vigorously overnight with 1×160 ml 0.5M sodium potassium tartrate
extractionThe mixture is extracted with 3×100 ml ethyl acetate
washThe combined organics are washed with 1×100 ml saturated sodium chloride
dry with materialdried over magnesium sulfate
concentrationThe organics are concentrated in vacuo to a crude amber oil (35 g)

Sources & evidence

ORD record: ord-bbbe0cecd57c465eaa811f634bf14b83
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05116981

Reaction notes

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