m-Chloroperbenzoic acid → Dibenzyl 2-[(benzylsulfinyl)methyl]pentanedioate

HRID 1937338Notes

Reaction equation

HRID 1937338 reaction equation
[CH2:1]([S:8]([CH2:11][CH:12]([CH2:23][CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])(=O)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=O)C=1>ClCCl>[CH2:1]([S:8]([CH2:11][CH:12]([CH2:23][CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])[C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 15410803HCID 15410803, compound

Product 1

HCID 22460508Dibenzyl 2-[(benzylsulfinyl)methyl]pentanedioateYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution (−78° C.) of dibenzyl 2-[(benzylsulfonyl)methyl]pentanedioate (8.2 g, 18.3 mmol) in dichloromethane (100 mL), was added 3-chloroperbenzoic acid (85%, 8.2 g, 40.3 mmol) with stirring. The reaction mixture was allowed to warm to room temperature. White solids precipitated from the reaction mixture. After 2 hours at room temperature, the reaction mixture was filtered and the white solids washed with dichloromethane. The filtrate was washed twice with a saturated aqueous solution of sodium bicarbonate and the dichloromethane removed under reduced pressure. The resulting oil was purified by column chromatography to yield 7.5 g (85%) of clear oil.

Workup

  1. customWhite solids precipitated from the reaction mixture
  2. filtrationthe reaction mixture was filtered
  3. washthe white solids washed with dichloromethane
  4. washThe filtrate was washed twice with a saturated aqueous solution of sodium bicarbonate
  5. customthe dichloromethane removed under reduced pressure
  6. customThe resulting oil was purified by column chromatography

Sources & evidence

ORD record
ord-02de639771e14feb908e13b10c533c25
Source dataset
uspto-grants-2002_05
Patent number
US06395718B1

Reaction notes

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