Tert-butyl 2-(bromomethyl)prop-2-enoate → 3-(1-Carboxycyclopentyl)-2-methylenepropanoic acid t-butyl ester

Participants

Reaction Steps

Cyclopentane carboxylic acid dilithio dianion (prepared from cyclopentane carboxylic acid (2.58 g) as described in Example 15) in tetrahydrofuran (100 ml) was treated with zinc chloride (1.85 g) at room temperature for 30 minutes, followed by t-butyl 2-bromomethylpropenoate (5.0 g) at -78° C. The reaction mixture was worked-up and the product purified as previously described to give 3-(1-carboxycyclopentyl)-2-methylenepropanoic acid t-butyl ester as an oil (5.1 g, 89%). Found: C,66.16; H,8.89. C14H22O4 requires C,66.11; H,8.72%.

Provenance & Evidence