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

HRID 1602526Notes

Reaction equation

HRID 1602526 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 3h. 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-27105d5a37b248b7a83e4330a1a411e7
Source dataset
uspto-grants-1999_11
Patent number
US05981576

Reaction notes

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