Pyridine → 4-Phenyl-2-indanyl cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate

HRID 444246Notes

Reaction equation

HRID 444246 reaction equation
[C:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH2:9][CH:10]([OH:16])[CH2:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[Cl:23][C:24]([C:34]([F:37])([F:36])[F:35])=[CH:25][C@@H:26]1[C@H:28]([C:29](Cl)=[O:30])[C:27]1([CH3:33])[CH3:32]>C1(C)C=CC=CC=1>[Cl:23][C:24]([C:34]([F:35])([F:36])[F:37])=[CH:25][C@@H:26]1[C@H:28]([C:29]([O:16][CH:10]2[CH2:9][C:8]3[C:12](=[CH:13][CH:14]=[CH:15][C:7]=3[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:11]2)=[O:30])[C:27]1([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 1049PyridineHCID 129423884-Phenyl-2,3-dihydro-1H-inden-2-olHCID 86737382cis-3-(2-Chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarbonyl chloride

Product 1

HCID 867377044-Phenyl-2-indanyl cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylateYield 25.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A stirred solution of 0.25 g (0.0012 mole) of 4-phenyl-2-indanol and 0.11 g (0.0014 mole) of pyridine in 10 ml of toluene was cooled to 5° C., and a solution of 0.28 g (0.0011 mole) of cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride, prepared in accordance with Example 8, in 5 ml of toluene was added portionwise. Upon complete addition the reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to a residual oil. The oil was placed on a silica gel pad, and the product was eluted with 50 ml of 1:1 hexane:toluene. The eluate was concentrated under reduced pressure at 100°-115° C./0.02 mm using a Kugelrohr distilling system to give 0.12 g of 4-phenyl-2-indanyl cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionwas added portionwise
  2. additionUpon complete addition the reaction mixture
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate concentrated under reduced pressure to a residual oil
  5. washthe product was eluted with 50 ml of 1:1 hexane
  6. concentrationThe eluate was concentrated under reduced pressure at 100°-115° C./0.02 mm
  7. distillationdistilling system

Sources & evidence

ORD record
ord-7f0272036a7a4203a28ca4cab1dab2f3
Source dataset
uspto-grants-1981_04
Patent number
US04263319

Reaction notes

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