Pyridine → (+)-4-Phenyl-2-indanyl (+)-cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

HRID 905384Notes

Reaction equation

HRID 905384 reaction equation
[Cl:1][C:2]([Cl:12])=[CH:3][C@@H:4]1[C@H:6]([C:7](Cl)=[O:8])[C:5]1([CH3:11])[CH3:10].[C:13]1([C:19]2[CH:27]=[CH:26][CH:25]=[C:24]3[C:20]=2[CH2:21][CH:22]([OH:28])[CH2:23]3)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]([Cl:12])=[CH:3][C@@H:4]1[C@H:6]([C:7]([O:28][CH:22]2[CH2:21][C:20]3[C:24](=[CH:25][CH:26]=[CH:27][C:19]=3[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:23]2)=[O:8])[C:5]1([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12617358cis-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropylcarbonyl chlorideHCID 129423884-Phenyl-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 86738413(+)-4-Phenyl-2-indanyl (+)-cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylateYield 65.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a manner similar to Example 12A, the reaction of 1.54 g (0.007 mole) of (+)-cis-3-(2,2-dichloroethenyl)-2,2-dimethyl-cyclopropanecarbonyl chloride and 1.5 g (0.007 mole) of (+)-4-phenyl-2-indanol (EE≥95%) in the presence of 0.7 g (0.009 mole) of pyridine and 20 ml of toluene gave 1.84 g of (+)-4-phenyl-2-indanyl (+)-cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate as an oil, EE≥95% (alcohol moiety). The nmr spectrum was consistent with the proposed structure.

Sources & evidence

ORD record
ord-ec9ac711d1a44056baebff99281cd474
Source dataset
uspto-grants-1983_12
Patent number
US04423255

Reaction notes

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