Pyridine → HCID 86740188, compound

HRID 370932Notes

Reaction equation

HRID 370932 reaction equation
[C:1]1([CH2:7][C@H:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C@H:10]([OH:17])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:18][C:19]([C:29]([F:32])([F:31])[F:30])=[CH:20][C@@H:21]1[C@H:23]([C:24](Cl)=[O:25])[C:22]1([CH3:28])[CH3:27].N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:18][C:19]([C:29]([F:30])([F:31])[F:32])=[CH:20][C@@H:21]1[C@H:23]([C:24]([O:17][C@H:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C@H:8]([CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:9]2)=[O:25])[C:22]1([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 13094019HCID 13094019, compoundHCID 86737382cis-3-(2-Chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarbonyl chloride

Product 1

HCID 86740188HCID 86740188, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In the manner of Example 4, the reaction of 0.6 g (0.0027 mole) of trans-3-phenylmethyl-1-indanol (96% trans, 4% cis) and 0.704 g (0.0027 mole) of cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride (which may be prepared by method disclosed in U.S. Pat. No. 4,238,505, Example 7) in the presence of 0.214 g (0.0027 mole) of pyridine and 50 mL of toluene gave 0.75 g of trans-3-phenylmethyl-1-indanyl cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate. The ir and nmr spectra were consistent with the proposed structure.

Workup

  1. custommay be prepared by method

Sources & evidence

ORD record
ord-4bc793faa6f14f208cda8d4cb60eb0d3
Source dataset
uspto-grants-1985_07
Patent number
US04528408

Reaction notes

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