Carbon Tetrachloride → HCID 21185183, compound

Participants

Reaction Conditions

Reaction Steps

From 27: A solution of 27 (55 mg, 0.16 mmol) in 3 mL anhydrous CH2Cl2 was treated with CCl4 (155 μL, 1.6 mmol) and Ph3P (212 mg, 0.81 mmol) and the mixture was stirred at 25° C. for 2 h. The solution was concentrated in vacuo. Flash chromatography (SiO2, 1.5×15 cm, 0-12% EtOAc/hexane gradient) provided 28 (52 mg, 90%) as a white solid: mp 99-101° C.; 1H NMR (CDCl3, 250 MHz) δ8.03 (br s, 1H), 7.89 (d, J=8.1 Hz, 1H), 7.72 (d, J=7.6 Hz, 1H), 7.37 (m, 2H), 5.24 (d, J=6.1 Hz, 1H), 5.15 (d, J=6.1 Hz, 1H), 4.06 (m, 4H), 3.65 (s, 3H), 3.51 (app t, J=10.1 Hz, 1H), 1.59 (s, 9H); 13C NMR (CDCl3, 100 MHz) δ152.3, 150.5, 141.1, 136.2, 127.9, 126.6, 124.6, 124.1, 122.4, 121.4, 107.7, 100.0, 81.2, 57.5, 52.1, 45.9, 40.8, 28.4; IR (film) νmax 2976, 1704, 1634, 1449, 1336, 1147, 1055, 983 cm−1; FABHRMS (NBA) m/z 378.1463 (C20H24ClNO4+H+ requires 378.1472).

Provenance & Evidence