Benzoyl chloride → HCID 70005219, compound

Participants

Reaction Steps

To a solution of benzoyl chloride (0.224 mL, 1.94 mmol) in tetrahydrofuran (20 mL) was added tris(dibenzylideneacetone)dipalladium(0) (Pd2(DBA)3) (8.8 mg, 0.01 mmol) and tri-2-furylphosphine (9.2 mg, 0.04 mmol). The mixture was stirred for 10 minutes and trans-7-[2-oxo-5-(2-tributylstannanyl-vinyl)-cyclopentyl]-heptanoic acid methyl ester (the compound of Preparation 1, Step D, 1.0 g, 1.85 mmol) was added. The reaction was stirred for 24 h and was concentrated in vacuo. Radial chromatography (hexanes to 20% hexanes in ethyl acetate) provided the title compound of Step A as a clear and colorless oil (569 mg). 1H NMR (CDCl3, 250 MHz) d 7.94 (m, 2H), 7.62-7.42 (m, 3H), 7.00 (m, 2H), 3.64 (s, 3H), 2.75 (m, 1H), 2.44 (m, 1H), 2.23 (m, 5H), 2.03 (m, 1H), 1.86-1.16 (m, 8H), 0.90 (t, 2H).

Provenance & Evidence