Water → HCID 18351618, compound

HRID 430794Notes

Reaction equation

HRID 430794 reaction equation
[C:1]1([CH:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[S:8][CH2:9][CH2:10][C:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[C:19]([O:20][CH2:21][C:22]([OH:24])=[O:23])[C:14]=3[O:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:39])C=1.[OH2:42]>ClCCl>[C:25]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[S:8]([CH2:9][CH2:10][C:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[C:19]([O:20][CH2:21][C:22]([OH:24])=[O:23])[C:14]=3[O:13][CH:12]=2)(=[O:39])=[O:42])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 11316066HCID 11316066, compound

Product 1

HCID 18351618HCID 18351618, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(3-(2-(diphenylmethyl)thioethyl)benzofuran-7-yloxy)acetic acid (126 mg) was dissolved in dichloromethane (2 ml) and the obtained solution was cooled to 0° C. To this solution, m-chloroperbenzoic acid (143 mg) was added and the resulting mixture was stirred for 2 hours. The reaction solution was poured into water layer (30 ml) and the resultant was extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with saturated aqueous sodium thiosulfate solution and with saturated brine, followed by drying over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=1/2+5% acetic acid) using silica gel to obtain the desired compound (97 mg, yield: 72%).

Workup

  1. extractionthe resultant was extracted twice with ethyl acetate (20 ml)
  2. washwashed with saturated aqueous sodium thiosulfate solution and with saturated brine
  3. dry with materialby drying over sodium sulfate
  4. customAfter removing the sodium sulfate
  5. filtrationby filtration
  6. customthe solvent was removed under reduced pressure
  7. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=1/2+5% acetic acid)

Sources & evidence

ORD record
ord-0a845299fe3141369cd38ffbe2c729b6
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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