HCID 13956721, compound → 2-Methyl-3-phenylbenzyl 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylate

HRID 1607367Notes

Reaction equation

HRID 1607367 reaction equation
[CH3:1][C:2]1([CH3:39])[CH:4]([CH:5](OC(=O)C2C=CC=CC=2)[C:6](Cl)([Cl:11])[C:7]([F:10])([F:9])[F:8])[CH:3]1[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:27]=1[CH3:38])=[O:23]>CN(C=O)C.[Zn]>[CH3:1][C:2]1([CH3:39])[CH:4]([CH:5]=[C:6]([Cl:11])[C:7]([F:8])([F:9])[F:10])[CH:3]1[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:27]=1[CH3:38])=[O:23]

Participants

4

Reactant 1

HCID 13956721HCID 13956721, compound

Product 1

HCID 549012-Methyl-3-phenylbenzyl 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylateYield 98%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 56 mg (0.097 mmol) of (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(1-benzoyloxy-2,2-dichloro-3,3,3-trifluoropropyl)cyclopropanecarboxylate obtained in Example 12 and dissolved in 0.1 ml of DMF, 8 mg (0.12 mmol) of zinc powder was added, and the mixture was stirred at 60° C. for 6 hours. The subsequent operation was carried out in the same manner as in Reference Example 9, whereby 40 mg of (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(2-chloro-3,3,3-trifluoro-1-propenyl)cyclopropanecarboxylate was obtained. Yield: 98%. (Z):(E)=86:14.

Sources & evidence

ORD record
ord-26a7236a49034cf5a4887b582da45817
Source dataset
uspto-grants-1989_09
Patent number
US04864052

Reaction notes

Loading…