Sulfuric Acid → 5-Methoxy-5-methyl-4-(4-(methylsulfonyl)phenyl)-3-phenyl-2-(5H)-furanone

HRID 2295098Notes

Reaction equation

HRID 2295098 reaction equation
[OH:1][C:2]1([CH3:24])[O:6][C:5](=[O:7])[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:3]1[C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1.OS(O)(=O)=O.[CH3:30]CN(CC)CC>CO>[CH3:30][O:1][C:2]1([CH3:24])[O:6][C:5](=[O:7])[C:4]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[C:3]1[C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8471TriethylamineHCID 214727535-Hydroxy-4-(4-methanesulfonyl-phenyl)-5-methyl-3-phenyl-5H-furan-2-one

Product 1

HCID 98851385-Methoxy-5-methyl-4-(4-(methylsulfonyl)phenyl)-3-phenyl-2-(5H)-furanone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-hydroxy-5-methyl-4-(4-(methylsulfonyl)phenyl)-3-phenyl-2-(5H)-furanone (Example 4) (1.0 g) in 120 mL of MeOH was added 0.1 mL of concentrated H2SO4. The mixture was heated to reflux for 3 days and then treated with 2 mL of Et3N. Methanol was removed under reduced pressure and the residue was purified by silica gel flash chromatography eluted with 4:1 toluene/EtOAc. After a swish from 2:1 hexane/EtOAc, 0.8 g of the title compound was obtained as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 days
  3. customMethanol was removed under reduced pressure
  4. customthe residue was purified by silica gel flash chromatography
  5. washeluted with 4:1 toluene/EtOAc

Sources & evidence

ORD record
ord-8ef8652a40004c6892818cc8eb7d31a1
Source dataset
uspto-grants-1997_11
Patent number
US05691374

Reaction notes

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