Dimethylformamide dimethyl acetal → (E)-1-(3-((tert-butyldimethylsilyloxy)methyl)pyridin-2-yl)-3-(dimethylamino)prop-2-en-1-one

HRID 1484764Notes

Reaction equation

HRID 1484764 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[C:11]([C:16](=[O:18])[CH3:17])=[N:12][CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CO[CH:21](OC)[N:22]([CH3:24])[CH3:23]>>[Si:1]([O:8][CH2:9][C:10]1[C:11]([C:16](=[O:18])/[CH:17]=[CH:21]/[N:22]([CH3:24])[CH3:23])=[N:12][CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 896547341-(3-((Tert-butyldimethylsilyloxy)methyl)pyridin-2-yl)ethanone

Product 1

HCID 86690729(E)-1-(3-((tert-butyldimethylsilyloxy)methyl)pyridin-2-yl)-3-(dimethylamino)prop-2-en-1-one

Procedure

1-(3-((tert-butyldimethylsilyloxy)methyl)pyridin-2-yl)ethanone (10.8 g, 40.75 mmol) in dimethoxy-N,N-dimethylmethanamine (15.0 mL) was heated to reflux for 3 days. The mixture was concentrated and used for next step without further purification. MS (ESI) m/z 321.1 [M+H]+.

Workup

  1. temperatureto reflux for 3 days
  2. concentrationThe mixture was concentrated
  3. customused for next step without further purification

Sources & evidence

ORD record
ord-1a3f9c7101bd473c8defadd295ffae42
Source dataset
uspto-grants-2016_08
Patent number
US09422279B2

Reaction notes

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