Pyridine → (RS)-3-isopropyl-4-methylidenecyclopenten-2-yl (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate

HRID 1379936Notes

Reaction equation

HRID 1379936 reaction equation
C(C1C(=C)CC([OH:10])C=1)(C)C.N1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl:17]/[C:18](/[C:28]([F:31])([F:30])[F:29])=[CH:19]\[C@@H:20]1[C@H:22]([C:23](Cl)=[O:24])[C:21]1([CH3:27])[CH3:26].[C:32]1([CH3:38])[CH:37]=CC=C[CH:33]=1>>[Cl:17]/[C:18](/[C:28]([F:31])([F:30])[F:29])=[CH:19]\[C@@H:20]1[C@H:22]([C:23]([O:10][C:12]2[CH:33]([CH:32]([CH3:38])[CH3:37])[C:15](=[CH2:16])[CH2:14][CH:13]=2)=[O:24])[C:21]1([CH3:27])[CH3:26]

Participants

5

Reactant 4

HCID 1049PyridineHCID 1140Toluene2×HCID 11334477(1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chlorideHCID 22908391(RS)-3-isopropyl-4-methylidenecyclopent-2-en-1-ol

Product 1

HCID 86749756(RS)-3-isopropyl-4-methylidenecyclopenten-2-yl (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylateYield 39%

Procedure

After 0.26 g of (RS)-3-isopropyl-4-methylidenecyclopent-2-en-1-ol was dissolved in 5 ml of toluene, 0.23 ml of pyridine was added to the toluene solution. Under ice-water cooling, 0.55 g of (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride was added dropwise to the mixed solution, and then stirred at an ambient temperature for six hours. The reaction solution was poured into ice-water and extracted with ethyl acetate. The ethyl acetate layer was washed successively with 5% aqueous hydrochloric acid, water, and a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After removal of the solvent under reduced pressure, the obtained oily substance was subjected to silica gel column chromatography to yield 0.25 g of (RS)-3-isopropyl-4-methylidenecyclopenten-2-yl (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate (Compound No.6). Yield 39% nD26 1.4804

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed successively with 5% aqueous hydrochloric acid, water
  3. dry with materiala saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  4. customAfter removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-5aed0796a69c4616a12bf71c82f0ef00
Source dataset
uspto-grants-1997_09
Patent number
US05672779

Reaction notes

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