m-Chloroperbenzoic acid → 2-[(2R)-Oxiran-2-ylmethoxy]-5-[(trifluoromethyl)sulfonyl]phenyl acetate

HRID 39012Notes

Reaction equation

HRID 39012 reaction equation
[O:1]1[CH2:3][C@@H:2]1[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13])=[CH:8][C:7]=1C(=O)C.C1C=C(Cl)C=[C:24]([C:29]([O:31]O)=[O:30])C=1>C(Cl)(Cl)Cl>[C:29]([O:31][C:7]1[CH:8]=[C:9]([S:12]([C:15]([F:16])([F:17])[F:18])(=[O:13])=[O:14])[CH:10]=[CH:11][C:6]=1[O:5][CH2:4][C@H:2]1[CH2:3][O:1]1)(=[O:30])[CH3:24]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 866529481-{2-[(2R)-Oxiran-2-ylmethoxy]-5-[(trifluoromethyl)sulfonyl]phenyl}ethanone

Product 1

HCID 866529492-[(2R)-Oxiran-2-ylmethoxy]-5-[(trifluoromethyl)sulfonyl]phenyl acetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Preparation according to Preparation 19 using 1-{2-[(2R)-oxiran-2-ylmethoxy]-5-[(trifluoromethyl)sulfonyl]phenyl}ethanone (1.2 g, 3.7 mmol) and m-CPBA (4.95 g, 22.5 mmol) in CHCl3 (50 ml). Crude yield 1.0 g. MS m/z (rel. intensity, 70 eV) 298 (34), 229 (77), 165 (bp), 107 (39), 79 (30).

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-6905ee7f6693420b9421b05e3dd2f47d
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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