Acetic Anhydride → Ethyl 2,2-dimethyl-3-(1-acetoxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate

HRID 1607359Notes

Reaction equation

HRID 1607359 reaction equation
[CH3:1][C:2]1([CH3:19])[CH:4]([CH:5]([OH:13])[C:6]([Cl:12])([Cl:11])[C:7]([F:10])([F:9])[F:8])[CH:3]1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[C:20](OC(=O)C)(=[O:22])[CH3:21]>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:19])[CH:4]([CH:5]([O:13][C:20](=[O:22])[CH3:21])[C:6]([Cl:11])([Cl:12])[C:7]([F:8])([F:9])[F:10])[CH:3]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13703173Ethyl 2,2-dimethyl-3-(1-hydroxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate

Product 1

HCID 13956726Ethyl 2,2-dimethyl-3-(1-acetoxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 305 mg (0.944 mmol) of ethyl 2,2-dimethyl-3(1-hydroxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate obtained in Example 2, 1 ml of pyridine and 1 ml of acetic anhydride, were added, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, and then purified by column chromatography (silica gel, dichloromethane/hexane=1/1) to obtain 322 mg of ethyl 2,2-dimethyl-3-(1-acetoxy-2,2-dichloro-3,3,3trifluoropropyl)cyclopropanecarboxylate (a mixture of two stereoisomers (55:45)) as a colorless oily substance.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified by column chromatography (silica gel, dichloromethane/hexane=1/1)

Sources & evidence

ORD record
ord-ef62c4c9d8de438499d9f421cd4b7b0b
Source dataset
uspto-grants-1989_09
Patent number
US04864052

Reaction notes

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