p-Toluenesulfonic acid → 2(5H)-Furanone, 3-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-

HRID 1376541Notes

Reaction equation

HRID 1376541 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)=O)=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:10])[O:11][CH2:12][C:13]=2[C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 189338812-(4-(Methylsulfonyl)phenyl)-2-oxoethyl 2-(4-fluorophenyl)acetate

Product 1

HCID 108303942(5H)-Furanone, 3-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-Yield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Under nitrogen, 4.10 g (11.7 mmol) of 2-(4-fluorophenyl)-1-[2-[4-(methylsulfonyl)phenyl]-2-oxoethoxy]ethanone (prepared in Step 4), 6.52 mL (46.8 mmol) of triethylamine, 4.89 g (25.7 mmol) of p-toluenesulfonic acid, and 12 g of 4Å molecular sieves were added to 117 mL of acetonitrile and stirred at reflux for 16 hours. The reaction mixture was concentrated in vacuo and the residue partitioned between dichloromethane and water. The dichloromethane layer was dried (MgSO4) and reconcentrated in vacuo. Recrystallization from hexane/ethyl acetate (2:1) gave 3.65 g (94%) of 3-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-5H-furan-2-one as a solid: mp 166°-167° C.; NMR (CDCl3) δ3.08 (s, 3H), 5.19 (s, 2H), 7.10 (t, J=9 Hz, 2H), 7.42 (dd, J=6 and 9 Hz, 2H), 7.52 (d, J=9 Hz, 2H), 7.97 (d, J=9 Hz, 2H); HRMS. Calc'd for C17H13FO45 : 332.0519. Found: 332.0501. Anal. Calc'd for C17H13FO45 : C, 61.44; H, 3.94; O, 19.26. Found: C, 61.11; H, 4.06; 0, 19.32.

Workup

  1. temperatureat reflux for 16 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue partitioned between dichloromethane and water
  4. dry with materialThe dichloromethane layer was dried (MgSO4)
  5. customRecrystallization from hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-c63dc2a8570545788e1429628c2d8b22
Source dataset
uspto-grants-1997_09
Patent number
US05663180

Reaction notes

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