2-(Diethyl amino)acetic acid 2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one-2-yl ester → 3-(Diethyl amino)-5,5-dimethyl-4-(4-(methylsulfonyl)phenyl)-5H-furan-2-one

HRID 1106599Notes

Reaction equation

HRID 1106599 reaction equation
[CH3:1][C:2]([O:16][C:17](=[O:24])[CH2:18][N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])([CH3:15])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)=O>CN(C=O)C.C(OCC)(=O)C>[CH2:20]([N:19]([CH2:22][CH3:23])[C:18]1[C:17](=[O:24])[O:16][C:2]([CH3:15])([CH3:1])[C:3]=1[C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1)[CH3:21]

Participants

4

Reactant 1

HCID 541051532-(Diethyl amino)acetic acid 2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one-2-yl ester

Product 1

HCID 219484443-(Diethyl amino)-5,5-dimethyl-4-(4-(methylsulfonyl)phenyl)-5H-furan-2-oneYield 31%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride, 60% dispersion (0.478 g, 11.96 mmol) was washed in hexane and suspended in DMF (5 mL). This suspension was added to a 0° C. solution of 2-(diethylamino)acetic acid 2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one-2-yl ester (1.70 g, 4.78 mmol) in DMF (20 mL). The resulting mixture was warmed to RT for 15 minutes. The mixture was diluted with ethyl acetate and quenched with water. The organic layer was washed with brine, dried over MgSO4 and concentrated to dryness. The residue was purified by swishing in ether/hexanes to give 500 mg of crystalline solid on filtration.

Workup

  1. washSodium hydride, 60% dispersion (0.478 g, 11.96 mmol) was washed in hexane
  2. customquenched with water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness
  6. customThe residue was purified

Sources & evidence

ORD record
ord-6e90ccc8bee542b8af8a051a549411d3
Source dataset
uspto-grants-2000_05
Patent number
US06057319

Reaction notes

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