Acetonitrile → HCID 68871458, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diethylmalonate (5.45 g, 0.034 mol) in 80 mL acetonitrile at 0° C. was added magnesium chloride (3.24 g, 0.034 mol) and triethylamine (10 mL, 0.066 mol). The slurry was stirred at 0° C. for fifteen minutes and then room temperature for two hours. The slurry was then cooled to 0° C. where a solution of Example 155D (0.034 mol) in 100 mL acetonitrile was added. The slurry was heated at 50° C. for 18 hours. The solvent was removed under vacuum and residue portioned between ethyl acetate and 1 N HCl. The organic layer was dried with anhydrous magnesium sulfate and concentrated to yield 14.0 grams of product. A sample was purified on silica using 25% ethyl acetate in hexane. 1H NMR (300 MHz, CDCl3): δ ppm 0.83 (d, J=6.25 Hz, 3H) 0.86 (d, J=6.62 Hz, 3H) 1.06 (m, 2H) 1.19 (ddd, J=12.69, 7.17, 6.99 Hz, 6H) 1.49 (s, 3H) 1.93 (dd, J=9.01, 7.91 Hz, 2H) 3.80 (s, 3H) 4.06 (m, 2H) 4.11 (q, J=7.11 Hz, 2H) 4.53 (s, 1H) 6.87 (m, 2H) 7.18 (m, 2H).

Provenance & Evidence