Chlorotrimethylsilane → HCID 86730346, compound

Participants

Reaction Conditions

Reaction Steps

1,2-Dibromoethane (0.286 mL, 3.32 mmol) was added to a suspension of zinc powder (2.12 g, 32.4 mmol) in tetrahydrofuran (10 mL) under nitrogen atmosphere at room temperature. The liquid mixture was stirred at 65° C. for 10 minutes. The reaction liquid was allowed to stand to cool to room temperature, then chlorotrimethylsilane (0.400 mL, 3.13 mmol) was added, and the mixture was stirred at room temperature for 30 minutes. A solution of tert-butyl 3-iodoazetidine-1-carboxylate described in Production Example 26-3 (5.91 g, 20.9 mmol) in tetrahydrofuran (10 mL) was added to the reaction liquid over 5 minutes, and the mixture was stirred at room temperature for 40 minutes (a solution A). A solution of iris(dibenzylideneacetone)dipalladium(0) (382 mg, 0.418 mmol) and tri-2-furylphosphine (402 mg, 1.73 mmol) in tetrahydrofuran (10 mL) was stirred under nitrogen atmosphere at room temperature for 15 minutes, and then the previously prepared solution A was added at room temperature. Subsequently, a solution of ethyl 4-iodobenzoate (6.92 g, 25.1 mmol) in tetrahydrofuran (18.5 mL) was added under nitrogen atmosphere at room temperature. The reaction liquid was stirred at 65° C. overnight. The reaction liquid was allowed to stand to cool to room temperature, then was filtered with celite, and the resultant was washed with ethyl acetate. The filtrate was washed serially with a saturated aqueous sodium bicarbonate solution and a saturated saline solution and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the filtrate was concentrated under vacuum. The residue was dissolved in dichloromethane, then the resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=9:1-4:1) to obtain the title compound (4.35 g, 68%).

Provenance & Evidence