m-Chloroperbenzoic acid → HCID 85815387, compound

HRID 584155Notes

Reaction equation

HRID 584155 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:18]=[CH:17][C:11]([O:12][CH:13]([CH3:16])[CH:14]=[CH2:15])=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:24]>ClCCl.C1(C)C=CC=CC=1>[O:24]1[CH:14]([CH:13]([O:12][C:11]2[CH:17]=[CH:18][C:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])=[CH:9][CH:10]=2)[CH3:16])[CH2:15]1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 858153853-[4-(tert-Butoxycarbonyl)phenoxy]-1-butene

Product 1

HCID 85815387HCID 85815387, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (3R and 3S)-3-[4-(tert-butoxycarbonyl)phenoxy]-1-butene (3.78 g, 15.2 mmol) in dry dichloromethane (50 ml) was treated at 22° C. with 3-chloroperoxybenzoic acid (4.8 g, 28.0 mmol) and the resulting mixture was stirred for 140 hours. The mixture was then diluted with toluene, washed with 5% sodium thiosulfate, sodium bicarbonate and dried (magnesium sulfate). Evaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate 2%) gave 3.53 g (87%) of the title material as an oil. 1H NMR indicated a 6:4 diastereoisomeric mixture which was used as such for the next step.

Workup

  1. washwashed with 5% sodium thiosulfate, sodium bicarbonate
  2. dry with materialdried (magnesium sulfate)
  3. customEvaporation of the solvent and chromatography of the residue on silica gel (elution toluene-ethyl acetate 2%)

Sources & evidence

ORD record
ord-e9c815bbfb4e485990ad421afe7b2a25
Source dataset
uspto-grants-2005_08
Patent number
US06924391B2

Reaction notes

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