Carbon Tetrachloride → HCID 68675195, compound

Participants

Reaction Steps

The 3-aza-claisen reaction was carried out according to the method of Walters et al. (1991) Tetrahedron Lett. 2: 179-182. Amide 49.3 (15.9 g, 36.2 mmol) and PPh3 (21 g, 80 mmol) were dissolved in anhydrous dichloromethane (160 mL). Et3N (12 g, 119.5 mmol) and CCl4 (18.4 g, 119.5 mmol) were added dropwise. The resulting mixture was stirred at room temperature overnight. The reaction was quenched with saturated brine (250 mL). The organic phase was extracted with ethyl acetate (50 mL×3). The combined organic phases were dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified via flash chromatography (25% ethyl acetate in hexanes) to yield 12.3 g of 49.4. 1H NMR (400 MHz) (CDCl3) δ 7.73 (4H, s); 7.70 (1H, s); 7.61-7.51 (3H, m); 7.41 (2H, d, J=8.9 Hz); 7.05 (2H, d, J=8.9 Hz); 5.76-5.72 (1H, m); 5.21-5.17 (4H, m); 2.71-2.59 (2H, m); 1.72 (3H, s).

Provenance & Evidence