HCID 11617199, compound → Diphenyl Ether

Participants

Reaction Steps

To a solution of morpholinone 2 (0.214 g, 0.750 mmol) in toluene (10 mL), Red-Al (65% solution in toluene, 1.5 mL) was added dropwise at 0° C. The reaction mixture was stirred at ice temperature for 4 h. Excess Red-Al was destroyed by dropwise addition of 2M NaOH solution (5 mL) and acidified to pH 2 with 6N HCl. The solution was neutralized with saturated NaHCO3 and extracted with toluene (2×10 mL). The combined organic extract was washed with brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the product was purified on a column of silica gel (ethyl acetate: methanol, 80:20) to give morpholine compound 3 as a colorless solid (Yield: 0.062 g, 31%), mp 156-158° C. 1H NMR (CDCl3) δ: 7.45-7.38 (m, 5H), 6.97 (m, 2H), 6.58 (m, 1H), 6.50 (d, 1H), 4.53 (d, 1H), 4.10 (m, 1H), 3.95 (m, 1H), 3.90 (m, 1H), 2.90 (m, 2H), 2.50 (m, 1H), 2.42 (m, 1H). MS (ES) m/z 285.98 [C17H19NO3+H]+. Analysis: Calcd for C17H19NO3 (0.5H2O) C, 69.37; H, 6.85; N, 4.76. Found: C, 69.68; H, 5.45; N, 4.44.

Provenance & Evidence