Pyridine → HCID 86738805, compound

HRID 354541Notes

Reaction equation

HRID 354541 reaction equation
[Cl:1][C:2]([C:12]([F:15])([F:14])[F:13])=[CH:3][C@@H:4]1[C@H:6]([C:7](Cl)=[O:8])[C:5]1([CH3:11])[CH3:10].[C:16]([C:18]1[C:19]([CH3:27])=[C:20]([CH2:25][OH:26])[C:21]([CH3:24])=[CH:22][CH:23]=1)#[N:17].N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]([C:12]([F:15])([F:14])[F:13])=[CH:3][C@@H:4]1[C@H:6]([C:7]([O:26][CH2:25][C:20]2[C:21]([CH3:24])=[CH:22][CH:23]=[C:18]([C:16]#[N:17])[C:19]=2[CH3:27])=[O:8])[C:5]1([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 13135248HCID 13135248, compoundHCID 86737382cis-3-(2-Chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarbonyl chloride

Product 1

HCID 86738805HCID 86738805, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride (4.28 g, 0.018 mole) was added dropwise to a cooled solution of (3-cyano-2,6-dimethylphenyl)-methanol (2.93 grams, 0.018 mole) and pyridine (1.5 grams, 0.02 mole) in toluene (100 ml), and the mixture was allowed to come to room temperature. The solution was poured over crushed ice and extracted with methylene chloride. The combined organic extracts were washed successively with water, 5% aqueous hydrochloric acid, water, and saturated aqueous sodium bicarbonate solution. The organic phase was dried with magnesium sulfate, filtered and the solvent evaporated. The residue was chromatographed on a silica gel column, elution with heptane, then heptane/methylene chloride to give (3-cyano-2,6-dimethylphenyl)methyl cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate (1.11 grams, mp 98°).

Workup

  1. customto come to room temperature
  2. additionThe solution was poured
  3. customover crushed ice
  4. extractionextracted with methylene chloride
  5. washThe combined organic extracts were washed successively with water, 5% aqueous hydrochloric acid, water, and saturated aqueous sodium bicarbonate solution
  6. dry with materialThe organic phase was dried with magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated
  9. customThe residue was chromatographed on a silica gel column, elution with heptane

Sources & evidence

ORD record
ord-53ea385d974549bfb8c7f69cfb812643
Source dataset
uspto-grants-1983_03
Patent number
US04375476

Reaction notes

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