m-Chloroperbenzoic acid → Hydrogen Peroxide

HRID 1786443Notes

Reaction equation

HRID 1786443 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][OH:8])=[O:6]>C(O)(=O)C.C(Cl)Cl.CCOCC>[OH:7][OH:8].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][OH:8])=[O:6]

Participants

6

Reactant 1

HCID 70297m-Chloroperbenzoic acid

Product 2

HCID 784Hydrogen PeroxideHCID 70297m-Chloroperbenzoic acid

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Compound 20 is treated with an organolithium base (e.g. LDA, t-BuLi or, preferably, n-BuLi) at low temperature (preferably −78° C.) in a solvent such as DME, Et2O or, preferably, THF, followed by treatment with an organo-disulfide, preferably diphenyldisulfide, to afford compound 28. Compound 29 is obtained by treating compound 28 with a base (e.g. LHMDS, LDA or, preferably, LTMP) at low temperature (preferably −78° C.) in a solvent such as THF, followed by aldehyde RMCHO. Compound 29 is treated with an oxidizing agent (e.g. KMnO4, PCC, PDC, “Swern” oxidation reagents such as (COCl)2/DMSO/Et3N or, preferably, MnO2 in CH2Cl2) to yield compound 30, which is treated with an oxidizing agent (e.g.hydrogen peroxide in acetic acid, 3-chloroperoxybenzoic acid in CH2Cl2, or, preferably, 3-chloroperoxybenzoic acid in Et2O) to provide compound 31. Desired compound 25 of the present invention is obtained upon treatment of compound 31 with H-A3-L3-Q3 in the presence of a base (e.g. KH or, preferably, NaH) in a solvent such as DMF, benzene, DME or, preferably, THF.

Workup

  1. additionis treated with an oxidizing agent (e.g

Sources & evidence

ORD record
ord-a4908fc6925844869e9b5798da573048
Source dataset
uspto-grants-2009_03
Patent number
US07507756B2

Reaction notes

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