Acetic Acid → HCID 86176832, compound

Participants

Reaction Steps

A solution of 1,4-dioxaspiro[4.5]decan-8-one (5 g, 32.0 mmol), tert-butyl 2-cyanoacetate (4.97 g, 35.2 mmol), ammonium acetate (0.2 g) and acetic acid (1.0 mL) in toluene (75 ml) was refluxed using Dean-Stark water separator to isolate water formed for 16 hours. After cooling, the reaction mixture was washed twice with water, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material (4.18 g, 14.96 mmol) was treated with acetic acid (80% in water, 42.8 mL, 599 mmol) at 65° C. overnight. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography on Analogix IntelliFlash280 eluting with 5 to 100% ethyl acetate/hexanes to give the title compound. 1H NMR (501 MHz, CDCl3) δ 1.54 (s, 9H), 2.49-2.62 (m, 4H), 3.05-3.16 (m, 2H), 3.37 (t, J=7.0 Hz, 2H).

Provenance & Evidence