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

HRID 647324Notes

Reaction equation

HRID 647324 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 acetate-hexane. 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-c84562d34e5747deab3be71901b6e2de
Source dataset
uspto-grants-1983_10
Patent number
US04408057

Reaction notes

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