Ethyl diazoacetate → Ethyl 2-[2-({[4-(trifluoromethyl)phenyl]sulfonyl}oxy)phenyl]cyclopropanecarboxylate

HRID 1795122Notes

Reaction equation

[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:19]=[CH2:20])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[N+](=[CH:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N-]>>[F:22][C:2]([F:1])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:19]2[CH2:20][CH:25]2[C:26]([O:28][CH2:29][CH3:30])=[O:27])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

Reactant 2

HCID 12192Ethyl diazoacetate

HCID 221855252-Vinylphenyl 4-(trifluoromethyl)benzenesulfonate

Product 1

HCID 22185568Ethyl 2-[2-({[4-(trifluoromethyl)phenyl]sulfonyl}oxy)phenyl]cyclopropanecarboxylateYield 50%

Conditions

Temperature: 135 °C

Procedure

A mixture of 2-vinylphenyl 4-(trifluoromethyl)benzenesulfonate (1.8 g, 5.5 mmol) and ethyl diazoacetate (0.70 mL, 6.7 mmol) under argon is heated at 135° C. for 90 min. The product is purified on silica gel in methylene chloride and ethyl acetate-methylene chloride mixtures. The product, ethyl 2-[2-({[4-(trifluoromethyl)phenyl]sulfonyl}oxy)phenyl]cyclopropanecarboxylate, is obtained as a mixture of isomers. A yield of 50% is obtained.

Workup

customThe product is purified on silica gel in methylene chloride and ethyl acetate-methylene chloride mixtures

Sources & evidence

ORD record: ord-72101f7d3d8b489ea0e43a0bea3d753b
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07026339B2

Reaction notes

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