Triethylsilane → Diethyl 2-acetamido-2-(6-octyl-1,2,3,4-tetrahydronaphthalen-2-yl)malonate

Participants

Reaction Conditions

Reaction Steps

To a solution of triethylsilane (1.3 ml, 8.2 mmol) in 5 ml of CH2Cl2 was added compound 5 (1 g, 2.1 mmol) in 5 ml of CH2Cl2. The reaction mixture was stirred at room temperature under Ar and TiCl4 (0.09 ml, 8.2 mmol) was added dropwise. The resulting solution was stirred for 12 hours, cooled to 0° C. and quenched by slow addition of 10 ml of saturated NaHCO3. The aqueous layer was extracted with CH2Cl2 (3×30 mL). The combined organic layers were washed with brine (2×30 mL) and dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography (Silica gel, 20% EtOAc in hexanes) to provide 630 mg of compound 6 (65%).

Provenance & Evidence