Ethyl Acetate → HCID 178527209, compound

HRID 1601381Notes

Reaction equation

HRID 1601381 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[CH:11]=[CH:12]/[C@H:13]2[CH2:18][CH2:17][C@H:16]([S:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)[CH2:15][CH2:14]2)=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:38])C=1.S([O-])([O-])=O.[Na+].[Na+].C(OCC)(=O)C>C(Cl)Cl>[F:29][C:2]([F:1])([F:28])[C:3]1[CH:4]=[CH:5][C:6](/[CH:9]=[CH:10]/[CH:11]=[CH:12]/[C@H:13]2[CH2:14][CH2:15][C@H:16]([S:19]([CH2:20][C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=3)=[O:38])[CH2:17][CH2:18]2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 178506156HCID 178506156, compound

Product 1

HCID 178527209HCID 178527209, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 20 ml of methylene chloride were dissolved 211 mg (0.48 mmol) of 4-chlorobenzyl trans-4-[(1E,3E)-4-[4-(trifluoromethyl)phenyl]-1,3-butadienyl]cyclohexyl sulfide, and 104 mg (0.48 mmol) of m-chloroperbenzoic acid (purity: 80%) were added to the solution at 0° C., followed by stirring of the resulting mixture for 5 minutes. An aqueous sodium sulfite solution and ethyl acetate were added to the reaction mixture and the organic layer was washed with an aqueous sodium hydrogencarbonate solution and an aqueous NaCl solution. After the mixture was dried, the crude product obtained by evaporation of the solvent was recrystallized from a mixed solvent of ethyl acetate-hexane to obtain 168 mg (yield: 77%) of the title compound having a melting point of 212 to 214° C.

Workup

  1. additionwere added to the solution at 0° C.
  2. washthe organic layer was washed with an aqueous sodium hydrogencarbonate solution
  3. customAfter the mixture was dried
  4. customthe crude product obtained by evaporation of the solvent
  5. customwas recrystallized from a mixed solvent of ethyl acetate-hexane

Sources & evidence

ORD record
ord-1b80528a47734b3aa76235941388330d
Source dataset
uspto-grants-1999_11
Patent number
US05977152

Reaction notes

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