Phosgene → HCID 10863743, compound

Participants

Reaction Steps

To a stirred mixture of 2-11 (11.8 mmol), CH2Cl2 (3 mL) and 20% K2CO3 was added phosgene (1.93 M toluene, 6.7 ml, 13.0 mmol) dropwise over 20 minutes. After stirring for 30 minutes, the organic layer was separated and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 5-10% methanol/ethyl acetate) to give 2-12 as a yellow oil. TLC Rf =0.25 (silica, 70:20:10 chloroform/ethyl acetate/methanol) 1H NMR (300 MHz, CDCl3) δ 7.12 (d, J=7.6 Hz, 1H), 7.02 (d, J=7.3 Hz, 1H), 6.80 (d, J=7.6 Hz, 1H), 6.70 (s, 1H), 6.34 (d, J=7.3 Hz, 1H), 5.46 (t, J=7.9 Hz, 1H), 4.74 (s, 1H), 4.55 (t, J=8.9 Hz,2H), 4.10 (q, J=7.3 Hz, 2H), 3.41 (m, 2H), 3.21 (m, 6H), 2.95 (m,3H), 2.67(t, J=6.1 Hz, 2H), 2.52 (t, J=7.6 Hz, 2H), 1.88 (m, 5H), 1.20 (t, J=7.3 Hz, 3H).

Provenance & Evidence