Hydrochloric Acid → 5,5-dimethyl-3-(3-fluorophenyl)-4-(4-methylsulfonyl)phenyl-2(5H)-furanone

HRID 1106578Notes

Reaction equation

HRID 1106578 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][C:12]([CH3:26])([CH3:25])[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:5]=[CH:6][CH:7]=1.C1CCN2C(=NCCC2)CC1.Cl>C(Cl)Cl>[CH3:25][C:12]1([CH3:26])[O:11][C:9](=[O:10])[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[C:13]1[C:15]1[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 572652353-Fluorophenylacetic acid, 1,1-dimethyl-2-(4-(methylsulfonyl)phenyl)-2-oxo-ethyl ester

Product 1

HCID 99068925,5-dimethyl-3-(3-fluorophenyl)-4-(4-methylsulfonyl)phenyl-2(5H)-furanoneYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product from Step 2 (120 g) in CH2Cl2 (1 L) was treated with DBU (81.6 g) and stirred for 1 h at r.t. The reaction mixture was then treated with 1 M HCl (550 mL) and the organic phase was separated, washed with saturated NaHCO3 and dried over MgSO4. After concentration, the crude was swished from 20% EtOAc/hexanes (450 mL) to give the title compound as a white solid (108.4 g, m.p. 172.7° C.).

Workup

  1. customthe organic phase was separated
  2. washwashed with saturated NaHCO3
  3. dry with materialdried over MgSO4
  4. concentrationAfter concentration

Sources & evidence

ORD record
ord-1e2a55e1571547e9809572c38f1c2ff5
Source dataset
uspto-grants-2000_05
Patent number
US06057319

Reaction notes

Loading…