Water → 4-Benzyloxy-1-[2-(4-hydroxymethyl-2-methyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one

HRID 1425736Notes

Reaction equation

HRID 1425736 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([CH2:32][OH:33])=[CH:28][C:27]=1[CH3:34])=[O:25].O>CS(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:23][C:24]([C:26]2[CH:31]=[CH:30][C:29]([CH2:32][OH:33])=[CH:28][C:27]=2[CH3:34])=[O:25])[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 866955352-Bromo-1-(4-hydroxymethyl-2-methyl-phenyl)-ethanone

Product 1

HCID 866955374-Benzyloxy-1-[2-(4-hydroxymethyl-2-methyl-phenyl)-2-oxo-ethyl]-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-benzyloxy-1H-pyridin-2-one (728 mg, 3.62 mmol) in DMSO (4.00 mL) is added cesium carbonate (2.95 g, 9.05 mmol) and the mixture is stirred 15 min at room temperature. 2-Bromo-1-(4-hydroxymethyl-2-methyl-phenyl)-ethanone (preparation 1b, 880 mg, 3.62 mmol) is added in portions and the mixture and is stirred 2 h at room temperature. After addition of water, the precipitate is collected, washed with water and dried.

Workup

  1. stirringthe mixture and is stirred 2 h at room temperature
  2. customthe precipitate is collected
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-5b707981018f4f728524e01a5f52f210
Source dataset
uspto-grants-2015_01
Patent number
US08933079B2

Reaction notes

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