Acetaldehyde → N-[6-(1-Hydroxyethyl)pyridin-2-yl]-2,2-dimethylpropanamide

HRID 1042335Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[CH:20](=[O:22])[CH3:21]>C1COCC1>[OH:22][CH:20]([C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH:5]=[CH:4][CH:3]=1)[CH3:21]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of N-(6-bromopyridin-2-yl)-2,2-dimethylpropanamide (2 g, 7.77 mmol, 1 eq.) in 25 ml of THF was cooled to −78° C. and n-BuLi (1.6 M, 9.72 ml, 15.55 mmol) was added dropwise. After 1 h, acetaldehyde (0.376 g, 8.55 mmol, 1.1 eq.) was added and the mixture was warmed to 0° C. within 1 h. The reaction was quenched with H2O, and diluted with EtOAc. The aqueous layer was separated and extracted with EtOAc. The organics were combined, dried over MgSO4 and concentrated. The crude material was purified by chromatography on silica gel to give N-[6-(1-hydroxyethyl)pyridin-2-yl]-2,2-dimethylpropanamide (1.45 g, 83% yield) as a white solid.

Workup

customThe reaction was quenched with H2O
additiondiluted with EtOAc
customThe aqueous layer was separated
extractionextracted with EtOAc
dry with materialdried over MgSO4
concentrationconcentrated
customThe crude material was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-d8d64177ef044a50b4a08c346cfa3034
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557849B2

Reaction notes

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