Chlorotrimethylsilane → HCID 9865535, compound

Participants

Reaction Conditions

Reaction Steps

A 1.3 M solution of methyllithium (0.78 mL, 1.04 mmol) was added to a stirring suspension of copper (1) bromide-dimethyl sulfide (107 mg, 0.52 mmol) and 2 mL of THF at −78° C. The solution was warmed to −40° C. over 30 minuts and then re-cooled to −78° C. Freshly distilled hexamethylphosphoramide (0.091 mL, 0.52 mmol) was added, and the solution was stirred at −78° C. for 30 minutes. A solution of ethyl 4-(4-(2-methyl-6-oxocyclohex-1-enyl)but-3-en-1-ynyl)benzoate (Compound H, 80 mg, 0.26 mmol), chlorotrimethylsilane (0.07 mL, 3.94 mmol) and 2.5 mL of THF was added. After the solution was stirred at −78° C. for 1 hour, pyridine (0.020 mL) and ether (0.065 mL) were added. The reaction was then quenched by the addition of 5% aqueous NaHCO3. The layers were separated and the aqueous layer was extracted 3 times with ethyl acetate. The solvents were removed under reduced pressure, and the residue was purified by silica gel chromatography (10:1, hexane:ethyl acetate) to give the title compound as a yellow solid.

Provenance & Evidence