2,3-Dihydrofuran → HCID 66735283, compound

HRID 645303Notes

Reaction equation

HRID 645303 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:22]([F:25])([F:24])[F:23])=[CH:10][C:11]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][CH:14]=2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[O:26]1[CH:30]=[CH:29][CH2:28][CH2:27]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:22]([F:25])([F:23])[F:24])=[CH:10][C:11]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH:19][CH:27]3[CH2:28][CH2:29][CH2:30][O:26]3)=[O:18])=[CH:15][CH:14]=2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 709342,3-DihydrofuranHCID 521998p-Toluenesulfonic acid monohydrateHCID 66735592HCID 66735592, compound

Product 1

HCID 66735283HCID 66735283, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.25 g of 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)benzoic acid amide that was synthesized under Synthetic Example 9 in 3 mL of dichloromethane, 68 mg of 2,3-dihydrofuran and a catalytic amount of p-toluenesulfonic acid monohydrate were added and the mixture was stirred for 18 hours at room temperature. The solvent was distilled off from the reaction solution under reduced pressure, and the resulting residue was purified using silica gel column chromatography that was eluted with ethyl acetate-hexane (2:3) followed by crystallization from a mixed solvent of hexane and a small amount of ethyl acetate to obtain 0.12 g of aimed product as yellow solid.

Workup

  1. distillationThe solvent was distilled off from the reaction solution under reduced pressure
  2. customthe resulting residue was purified
  3. washwas eluted with ethyl acetate-hexane (2:3)
  4. customfollowed by crystallization from a mixed solvent of hexane

Sources & evidence

ORD record
ord-54e0e0e88d89496ea2a66552cf447732
Source dataset
uspto-grants-2010_04
Patent number
US07700808B2

Reaction notes

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