Cesium carbonate → 2,2-Dimethyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-3-oxo-propionic acid ethyl ester

HRID 2212560Notes

Reaction equation

HRID 2212560 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]([CH3:16])([CH3:15])[C:6]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)=[O:7])[CH3:2].Cl[CH2:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:23]=[C:22]([CH3:30])[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH2:1]([O:3][C:4](=[O:17])[C:5]([CH3:16])([CH3:15])[C:6]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[N:23]=[C:22]([CH3:30])[CH:21]=2)=[CH:12][CH:13]=1)=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 115357194-(Chloromethyl)-2-methylquinolineHCID 695963983-(4-Hydroxy-phenyl)-2,2-dimethyl-3-oxo-propionic acid ethyl ester

Product 1

HCID 695965072,2-Dimethyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-3-oxo-propionic acid ethyl esterYield 70%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The 3-(4-hydroxy-phenyl)-2,2-dimethyl-3-oxo-propionic acid ethyl ester (0.72 g, 3.07 mmol) was combined with 4-chloromethyl-2-methyl-quinoline (0.69 g, 3.07 mmol) and cesium carbonate (12.0 mmol) in DMSO under nitrogen at room temperature. The reaction was stirred for 24 h, filtered to remove the solids, and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give 2,2-dimethyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-3-oxo-propionic acid ethyl ester (0.82 g, 70%) as a viscous oil. MS found: (M+H)+=392.

Workup

  1. filtrationfiltered
  2. customto remove the solids
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3679d6263443462eb41dbe9ad59eab10
Source dataset
uspto-grants-2006_09
Patent number
US07102008B2

Reaction notes

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