m-Chloroperbenzoic acid → Ethyl 2-(4-cyclopropanesulfinylphenyl)-3-(tetrahydropyran-4-yl)acrylate

HRID 729699Notes

Reaction equation

HRID 729699 reaction equation
[CH:1]1([S:4][C:5]2[CH:10]=[CH:9][C:8]([C:11](=[CH:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=2)[CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:32])C=1>>[CH:1]1([S:4]([C:5]2[CH:6]=[CH:7][C:8]([C:11](=[CH:17][CH:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:10]=2)=[O:32])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67484543Ethyl 2-(4-cyclopropylsulfanylphenyl)-3-(tetrahydropyran-4-yl)acrylate

Product 1

HCID 68625275Ethyl 2-(4-cyclopropanesulfinylphenyl)-3-(tetrahydropyran-4-yl)acrylate

Procedure

Partial oxidation of ethyl 2-(4-cyclopropylsulfanylphenyl)-3-(tetrahydropyran-4-yl)acrylate (see Preparation 22, 3.14 g, 9.44 mmol) with mCPBA, employing the protocol described above in Preparation 18, furnished ethyl 2-(4-cyclopropanesulfinylphenyl)-3-(tetrahydropyran-4-yl)acrylate: m/z (ES+)=349.2 [M+H]+. Saponification of this ester (1.15 g, 3.3 mmol), using the procedure described in Preparation 25, afforded the title compound: m/z (ES+)=641.4 [2M+H]+.

Workup

  1. customdescribed above in Preparation 18

Sources & evidence

ORD record
ord-555e2d36c2834d7a847ef4818053747e
Source dataset
uspto-grants-2009_09
Patent number
US07582632B2

Reaction notes

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