Pyridine → 3-Chloro-1-cyclopropyl-1-(4-trifluoromethoxyphenyl)-1-propene

HRID 1110404Notes

Reaction equation

HRID 1110404 reaction equation
[CH:1]1([C:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=2)(O)[CH:5]=[CH2:6])[CH2:3][CH2:2]1.N1C=CC=CC=1.S(Cl)([Cl:27])=O>C(Cl)Cl>[Cl:27][CH2:6][CH:5]=[C:4]([CH:1]1[CH2:3][CH2:2]1)[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 150420281-Cyclopropyl-1-(4-trifluoromethoxyphenyl)-2-propen-1-ol

Product 1

HCID 537327453-Chloro-1-cyclopropyl-1-(4-trifluoromethoxyphenyl)-1-propeneYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under a nitrogen atmosphere a solution of 130.0 grams (0.5 mole) of 1-cyclopropyl-1-(4-trifluoromethoxyphenyl)-2-propen-1-ol and 49.3 grams (0.54 mole) of pyridine in 500 mL of methylene chloride was stirred, and 60.2 grams of thionyl chloride was added dropwise during a 30 minute period. The reaction mixture was maintained at 0° to 10° C. throughout the addition. Upon completion of addition the reaction mixture was stirred for 1 hour and then was diluted with 500 mL of methylene chloride and 500 mL of ice. The mixture was stirred until the ice melted. The organic layer was separated and was in turn washed with two 500 mL portions of aqueous 0.5N hydrochloric acid, two 500 mL portions of an aqueous solution saturated with sodium bicarbonate, two 500 mL portions of water, and two 500 mL portions of an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure yielding 113.5 grams of 3-chloro-1-cyclopropyl-1-(4-trifluoromethoxyphenyl)-1-propene.

Workup

  1. temperatureThe reaction mixture was maintained at 0° to 10° C. throughout the addition
  2. additionUpon completion of addition the reaction mixture
  3. customThe organic layer was separated
  4. washwashed with two 500 mL portions of aqueous 0.5N hydrochloric acid, two 500 mL portions of an aqueous solution saturated with sodium bicarbonate, two 500 mL portions of water, and two 500 mL portions of an aqueous solution saturated with sodium chloride
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-50785ae29a0341b7bb9250ae64d07194
Source dataset
uspto-grants-1990_12
Patent number
US04975451

Reaction notes

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