Acetic Acid → HCID 19856169, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the triflate from step A (500 mg, 1.60 mmol) and tetrakistriphenylphosphine palladium(0) (0.05 equiv, 92 mg, 0.08 mmol) in dry benzene (2 mL) under nitrogen at room temperature, a solution of sodium triisopropilsilanethiolate in dry tetrahydrofuran [1.3 equiv, prepared from triisopropilsilanethi61 (396 mg, 2.08 mmol) and sodium hydride (95%, 52 mg, 2.08 mmol) in tetrahydrofuran (2 mL) as in Example 22, Step B] was added and the reaction mixture was warmed to reflux (bath temp 90° C.) for 3.5 h. The reaction mixture was cooled down to 0° C. and tetrabutylammonium fluoride (1 M solution in tetrahydrofuran, 1.5 equiv, 3.1 mL, 3.1 mmol) and glacial acetic acid (3.5 equiv, 437 mg, 0.405 mL, 7.28 mmol) were added and the reaction mixture stirred at 0° C. for 20 min. Work-up as in Example 22, Step B gave, after flash chromatography (silica gel, hexane-ethyl acetate 25:1), the desired thiol as an oil (220 mg, 70%). The product was kept under nitrogen at −18° C.

Provenance & Evidence