m-Chloroperbenzoic acid → HCID 86650542, compound

HRID 2066639Notes

Reaction equation

HRID 2066639 reaction equation
[CH3:1][C:2](=[CH2:17])[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:8][CH:7]=1.ClC1C=CC=C(C(OO)=[O:26])C=1>>[CH3:17][C:2]1([CH2:3][O:4][CH2:5][C:6]2[CH:11]=[CH:10][C:9]([O:12][C:13]([F:14])([F:15])[F:16])=[CH:8][CH:7]=2)[CH2:1][O:26]1

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66955648HCID 66955648, compound

Product 1

HCID 86650542HCID 86650542, compoundYield 93%

Procedure

Epoxidation of alkene 121 with 3-chloroperbenzoic acid as in Example 2G, followed by chromatography of the product on silica gel, eluting with 0-15% CH2Cl2/petroleum ether (foreruns) and then with 15-75% CH2Cl2/petroleum ether and CH2Cl2, gave 2-methyl-2-({[4-(trifluoromethoxy)benzyl]oxy}methyl)oxirane (123) (93%) as an oil; 1H NMR (CDCl3) δ 7.37 (dt, J=8.7, 2.4 Hz, 2H), 7.19 (br d, J=7.9 Hz, 2H), 4.59 (d, J=12.1 Hz, 1H), 4.54 (d, J=12.1 Hz, 1H), 3.61 (d, J=11.1 Hz, 1H), 3.44 (d, J=11.1 Hz, 1H), 2.75 (d, J=4.9 Hz, 1H), 2.64 (d, J=4.9 Hz, 1H), 1.40 (s, 3H); HRCIMS (NH3) calcd for C12H17F3O3N m/z [M+H+NH3]+ 280.1161. found 280.1144.

Workup

  1. washeluting with 0-15% CH2Cl2/petroleum ether (foreruns)

Sources & evidence

ORD record
ord-9ca3ec86c82b4fa7b7d623a500a4dccc
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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