[Cl:1][C:2]([C:12]([F:15])([F:14])[F:13])=[CH:3][C@@H:4]1[C@H:6]([C:7](Cl)=[O:8])[C:5]1([CH3:11])[CH3:10].[C:16]([C:18]1[C:19]([CH3:27])=[C:20]([CH2:25][OH:26])[C:21]([CH3:24])=[CH:22][CH:23]=1)#[N:17].N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]([C:12]([F:15])([F:14])[F:13])=[CH:3][C@@H:4]1[C@H:6]([C:7]([O:26][CH2:25][C:20]2[C:21]([CH3:24])=[CH:22][CH:23]=[C:18]([C:16]#[N:17])[C:19]=2[CH3:27])=[O:8])[C:5]1([CH3:11])[CH3:10]Cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride (4.28 g, 0.018 mole) was added dropwise to a cooled solution of (3-cyano-2,6-dimethylphenyl)-methanol (2.93 grams, 0.018 mole) and pyridine (1.5 grams, 0.02 mole) in toluene (100 ml), and the mixture was allowed to come to room temperature. The solution was poured over crushed ice and extracted with methylene chloride. The combined organic extracts were washed successively with water, 5% aqueous hydrochloric acid, water, and saturated aqueous sodium bicarbonate solution. The organic phase was dried with magnesium sulfate, filtered and the solvent evaporated. The residue was chromatographed on a silica gel column, elution with heptane, then heptane/methylene chloride to give (3-cyano-2,6-dimethylphenyl)methyl cis-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate (1.11 grams, mp 98°).
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