1-Methylimidazole → 2,3,5,6-tetrafluorobenzyl (1R,3R)-3-((E)-Buta-1,3-dienyl)-2,2-dimethylcyclopropane-1-carboxylate

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Reaction Steps

In a similar way to that described in example 1 part b., 2.38 g (14.3 mmol) of (1R,3R)-3-((E)-buta-1,3-dienyl)-2,2-dimethylcyclopropane-1-carboxylic acid are added with 3.4 ml (43 mmol) of N-methyl imidazole dissolved in 43 ml of CH3CN, and reacted with 3.26 g (17.2 mmol) of tosyl chloride dissolved in 19 ml of CH3CN then with 2.6 ml (14.3 mmol) of 2,3,5,6-tetrafluorobenzyl alcohol dissolved in 16 ml of CH3CN. After purification on silica gel column with 100/1 (v/v) petroleum ether/ethyl ether as eluent, 4.58 g of an oily product with an E/Z ratio of 97/3 and a purity equal to 96.1% are obtained.

Provenance & Evidence