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

HRID 1940124Notes

Reaction equation

HRID 1940124 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 1M 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-23a4d75b605f49c2afef469f2d979168
Source dataset
uspto-grants-1997_12
Patent number
US05698584

Reaction notes

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