Triethylsilane → HCID 118324062, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of (E)-bis(4-chlorophenyl)(4-styrylquinolin-6-yl)methanol (18 mg, 0.0373 mmol) and triethylsilane (0.0238 mL, 0.149 mmol) in CH2Cl2 (1 mL) at −78° C. was dropwise added titanium chloride (0.0102 mL, 0.0933 mmol). The resulting mixture was warmed to 0° C. for 20 min. To the reaction was slowly added aq. NaHCO3, ice at 0° C. and CH2Cl2. 1N NaOH was added until the aqueous solution was basic. The aqueous layer was extracted with CH2Cl2 twice. The organics were concentrated and purified by silica column chromatography (20-25% EtOAc/hexanes). The product was found to contain ˜7% cis-isomer based on NMR. The resulting mixture was recrystallized from EtOAc/hexanes to remove the Cis isomer.

Provenance & Evidence