Pyridine → 4-(2-Thienyl)-2-indanyl cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate

HRID 325787Notes

Reaction equation

HRID 325787 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH2:8][CH:9]([OH:15])[CH2:10]2.N1C=CC=CC=1.[Cl:22][C:23]([C:33]([F:36])([F:35])[F:34])=[CH:24][C@@H:25]1[C@H:27]([C:28](Cl)=[O:29])[C:26]1([CH3:32])[CH3:31]>C1(C)C=CC=CC=1>[Cl:22][C:23]([C:33]([F:34])([F:35])[F:36])=[CH:24][C@@H:25]1[C@H:27]([C:28]([O:15][CH:9]2[CH2:8][C:7]3[C:11](=[CH:12][CH:13]=[CH:14][C:6]=3[C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[CH2:10]2)=[O:29])[C:26]1([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 1049PyridineHCID 131024634-(2-Thienyl)-2-indanolHCID 86737382cis-3-(2-Chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarbonyl chloride

Product 1

HCID 867387454-(2-Thienyl)-2-indanyl cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylateYield 43.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A stirred solution of 0.54 g (0.003 mole) of 4-(2-thienyl)-2-indanol and 0.25 g (0.003 mole) of pyridine in 15 mL of toluene was cooled to 5° C., and 0.65 g (0.003 mole) of cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarbonyl chloride in 5 mL of toluene was added dropwise. Upon complete addition, the reaction mixture was allowed to warm to ambient temperature where it was stirred for 16 hours. The reaction mixture was filtered, and the filtrate concentrated under reduced pressure to give an oil residue. The oil was subjected to column chromatography on silica gel, eluting with 100% hexane then 1% ethyl acetatehexane. The appropriate fractions were combined and concentrated under reduced pressure to give 0.57 g of 4-(2-thienyl)-2-indanyl cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate as an oil.

Workup

  1. additionUpon complete addition
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customto give an oil residue
  5. washeluting with 100% hexane
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea34bc88e7624a78abfa3527cd709b2d
Source dataset
uspto-grants-1984_04
Patent number
US04442296

Reaction notes

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