Water → HCID 12106051, compound

HRID 2394207Notes

Reaction equation

HRID 2394207 reaction equation
[CH3:1][C:2]1([CH3:31])[CH2:11][CH:10]=[C:9]([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]2[CH:7]=[C:6]([C:19]([O:21][C:22]3[CH:30]=[CH:29][C:25]([C:26]([OH:28])=[O:27])=[CH:24][CH:23]=3)=[O:20])[CH:5]=[CH:4][C:3]1=2.ClCl.[CH2:34]1COC[CH2:35]1.ClC1C=CC=C(C(OO)=[O:47])C=1.[OH2:50]>>[CH3:1][C:2]1([CH3:31])[CH2:11][CH:10]=[C:9]([S:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:47])=[O:50])[C:8]2[CH:7]=[C:6]([C:19]([O:21][C:22]3[CH:23]=[CH:24][C:25]([C:26]([O:28][CH2:34][CH3:35])=[O:27])=[CH:29][CH:30]=3)=[O:20])[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 24526ChlorineHCID 70297m-Chloroperbenzoic acidHCID 15887396HCID 15887396, compound

Product 1

HCID 12106051HCID 12106051, compound

Procedure

To a solution of 4-[[(5,5-dimethyl-5,6-dihydro-8-(phenylthio)-naphthalen-2-yl)carbonyl]oxy]-benzoic acid (Compound E26, 50.0 mg, 0.116 mmol) in 3.0 mL CH2 Cl2, and 1.0 mL THF at 0° C. was added m-chloroperbenzoic acid (57-80%) (34-52 mg, 0.197-0.299 mmol). The resulting solution was warmed to room temperature and stirred overnight. Water was added and the mixture extracted with EtOAc. The combined organic layers were washed with H2O and saturated aqueous NaCl before being dried over Na2SO4. Removal of the solvents under reduced pressure and crystallization of the residue from CH3CN 9 afforded the title compound as a colorless solid.

Workup

  1. extractionthe mixture extracted with EtOAc
  2. washThe combined organic layers were washed with H2O and saturated aqueous NaCl
  3. dry with materialbefore being dried over Na2SO4
  4. customRemoval of the solvents
  5. customunder reduced pressure and crystallization of the residue from CH3CN 9

Sources & evidence

ORD record
ord-3b7ddc96d83347e59364fef8da77e90a
Source dataset
uspto-grants-1998_09
Patent number
US05808124

Reaction notes

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