m-Chloroperbenzoic acid → HCID 67926552, compound

HRID 982482Notes

Reaction equation

HRID 982482 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([S:15]([C:18]1[CH:19]=[C:20]([C@H:36]2[CH2:40][CH2:39][C@H:38]([C:41]3[CH:46]=[C:45]([O:47][CH3:48])[C:44]([O:49][CH3:50])=[C:43]([O:51][CH3:52])[CH:42]=3)[O:37]2)[CH:21]=[C:22]([O:34][CH3:35])[C:23]=1[O:24][CH2:25][CH2:26][S:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:17])=[O:16])[CH2:13][CH3:14]>ClCCl>[CH2:12]([S:15]([C:18]1[CH:19]=[C:20]([C@H:36]2[CH2:40][CH2:39][C@H:38]([C:41]3[CH:42]=[C:43]([O:51][CH3:52])[C:44]([O:49][CH3:50])=[C:45]([O:47][CH3:48])[CH:46]=3)[O:37]2)[CH:21]=[C:22]([O:34][CH3:35])[C:23]=1[O:24][CH2:25][CH2:26][S:27]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:9])(=[O:16])=[O:17])[CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67907102HCID 67907102, compound

Product 1

HCID 67926552HCID 67926552, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

m-Chloroperbenzoic acid (50 mg, 1.1 eq) was added to a solution of trans-2-[3-propylsulfonyl-4-{2-(phenylthio)ethoxy}-5-methoxyphenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (300 mg) in dichloromethane (3 mL), and the mixture was stirred at room temperature for 1 h. The solid was filtered off and the filtrate was washed with 1N NaOH, dried, and concentrated to a residue. Purification by flash column chromatography (hexane-ethyl acetate 1:2) afforded the title compound.

Workup

  1. filtrationThe solid was filtered off
  2. washthe filtrate was washed with 1N NaOH
  3. customdried
  4. concentrationconcentrated to a residue
  5. customPurification by flash column chromatography (hexane-ethyl acetate 1:2)

Sources & evidence

ORD record
ord-0e3b1fa0d9a04c9595e615b5ea44924e
Source dataset
uspto-grants-1991_02
Patent number
US04996203

Reaction notes

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