Pyridine → 2,4,6-Trifluorophenylmethyl cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate

HRID 845503

Reaction equation

HRID 845503 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[CH2:10][OH:11].N1C=CC=CC=1.[Cl:18][C:19]([C:29]([F:32])([F:31])[F:30])=[CH:20][C@@H:21]1[C@H:23]([C:24](Cl)=[O:25])[C:22]1([CH3:28])[CH3:27].C(Cl)(Cl)=O>C1(C)C=CC=CC=1>[Cl:18][C:19]([C:29]([F:30])([F:31])[F:32])=[CH:20][C@@H:21]1[C@H:23]([C:24]([O:11][CH2:10][C:3]2[C:2]([F:1])=[CH:7][C:6]([F:8])=[CH:5][C:4]=2[F:9])=[O:25])[C:22]1([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 27770372,4,6-Trifluorobenzyl alcoholHCID 86737382cis-3-(2-Chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarbonyl chloride

Product 1

HCID 867422752,4,6-Trifluorophenylmethyl cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylateYield 11.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 1.5 grams (0.009 mole) of 2,4,6-trifluorophenylmethyl alcohol and 0.8 gram (0.01 mole) of pyridine in 30 ml of toluene was warmed to 50° and 2.4 grams (0.009 mole) of cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride was added. The addition caused a solid precipitate to form in the reaction mixture. Upon completion of the addition of the carbonyl chloride, the reaction mixture was heated under reflux for two hours, then allowed to cool to ambient temperature as it was stirred for 16 hours. The reaction mixture was placed on a column of 100 grams of silica gel and eluted with toluene. The appropriate fractions were combined and concentrated under reduced pressure to a clear residual oil. The residual oil was distilled under reduced pressure using a Kugelrohr distilling system. The appropriate fractions were combined to give 0.4 gram of 2,4,6-trifluorophenylmethyl cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate as an oil; nD25 1.4681.

Workup

  1. additionThe addition
  2. customto form in the reaction mixture
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for two hours
  5. washeluted with toluene
  6. concentrationconcentrated under reduced pressure to a clear residual oil
  7. distillationThe residual oil was distilled under reduced pressure
  8. distillationdistilling system

Sources & evidence

ORD record
ord-6ab4f4a8c7674ea292c2ed47e85b0cfc
Source dataset
uspto-grants-1988_07
Patent number
US04758590

Linked notes

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