Triethylamine → 5-Hydroxy-4-(4-methanesulfonyl-phenyl)-5-methyl-3-phenylsulfanyl-5H-furan-2-one

HRID 1940142Notes

Reaction equation

HRID 1940142 reaction equation
Br[CH:2]([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.[S:16]([CH2:23][C:24]([OH:26])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C.BrC(Br)=[O:36].C1CCN2C(=NCCC2)CC1>C(#N)C>[OH:36][C:2]1([CH3:15])[O:25][C:24](=[O:26])[C:23]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[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

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 59541(Phenylthio)acetic acidHCID 79057Carbonyl bromideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 132078392-Bromo-1-[4-(methanesulfonyl)phenyl]propan-1-one

Product 1

HCID 154615225-Hydroxy-4-(4-methanesulfonyl-phenyl)-5-methyl-3-phenylsulfanyl-5H-furan-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 2-bromo-1-(4-(methylsulfonyl)phenyl)propan-1-one (6.0 g, 20.6 mmol) and thiophenoxyacetic acid (3.8 g, 22.6 mmol) in acetonitrile (60 mL) was added triethylamine (4.0 mL, 28.8 mmol). The mixture was stirred at r.t. for 3 h. T.L.C. showed no bromoketone remaining and DBU (4.0 mL) was added. The mixture was stirred at r.t. for 1 h., then air was bubbled through the mixture for another hour. After dilution with water, the mixture was extracted with EtOAc. The EtOAc extract was washed with 1N aquous HCl, brine, dried over MgSO4, filtered and the solvent evaporated under vacuum. The residue was swished in Et2O to give the title compound (6.0 g) as a pale yellow powder.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at r.t. for 1 h.
  3. customair was bubbled through the mixture for another hour
  4. extractionAfter dilution with water, the mixture was extracted with EtOAc
  5. extractionThe EtOAc extract
  6. washwas washed with 1N aquous HCl, brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-f03d19bc729a491a84cdba226513086a
Source dataset
uspto-grants-1997_12
Patent number
US05698584

Reaction notes

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