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
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
Product 1
Reagents, catalysts & solvents 2
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.