1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-(3,4-Difluorophenoxy)-5,5-dimethyl-4-(4-(methylsulfonyl)phenyl)-5H-furan-2-one

HRID 1602517Notes

Reaction equation

HRID 1602517 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[F:13])[O:5][CH2:6][C:7]([OH:9])=[O:8].O[C:15]([CH3:29])([CH3:28])[C:16]([C:18]1[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1)=O.C1CCN2C(=NCCC2)CC1>CN(C1C=CN=CC=1)C.ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[F:13])[O:5][C:6]1[C:7](=[O:9])[O:8][C:15]([CH3:29])([CH3:28])[C:16]=1[C:18]1[CH:19]=[CH:20][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 3029152-(3,4-Difluorophenoxy)acetic acidHCID 154285142-Hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one

Product 1

HCID 99086243-(3,4-Difluorophenoxy)-5,5-dimethyl-4-(4-(methylsulfonyl)phenyl)-5H-furan-2-one

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3,4-difluorophenoxyacetic acid (0.51 g, 2.73 mmol), 2-hydroxy-2-methyl-1-(4-(methylsulfonyl)phenyl)propan-1-one (0.5g, 2.1 mmol, Step 3), CMC (1.13 g, 2.73 mmol) and DMAP (15 mg, 0.10 mmol) in dichloromethane (12 ml) was stirred at r.t. for 18 hrs. Then, DBU (0.63 ml, 4.2 mmol) was added and the reaction mixture was refluxed for 3 h. After cooling to r.t. the mixture was extracted with ethyl acetate and washed successively with water, 1 N HCl and brine. The organic layer was dried over MgSO4, filtered and the solvent evaporated under vacuum. The residue was triturated in a mixture of ethyl acetate and hexane affording the title compound as a solid. M.P.: 93-95 ° C.

Workup

  1. temperaturethe reaction mixture was refluxed for 3 h
  2. extractionwas extracted with ethyl acetate
  3. washwashed successively with water, 1 N HCl and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent evaporated under vacuum
  7. customThe residue was triturated in a mixture of ethyl acetate and hexane affording the title compound as a solid

Sources & evidence

ORD record
ord-353d4ba5460846ac9672d891cefe55ac
Source dataset
uspto-grants-1999_11
Patent number
US05981576

Reaction notes

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