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

HRID 905379Notes

Reaction equation

HRID 905379 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.[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].N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:17][C:18]([C:28]([F:29])([F:30])[F:31])=[CH:19][C@@H:20]1[C@H:22]([C:23]([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:24])[C:21]1([CH3:27])[CH3:26]

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 61.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In the manner of Example 12A, the reaction of 1.5 g (0.007 mole) of (+)-4-phenyl-2-indanol (EE≥95%) and 1.77 g (0.007 mole) of (+)-cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride in the presence of 0.7 g (0.009 mole) of pyridine and 20 ml of toluene gave 1.87 g of (+)-4-phenyl-2-indanyl (+)-cis-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate as an oil, EE≥95% (alcohol moiety). The nmr spectrum was consistent with the proposed structure.

Sources & evidence

ORD record
ord-0d940a221e5b479ebebf47fed470aedc
Source dataset
uspto-grants-1983_12
Patent number
US04423255

Reaction notes

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