Water → HCID 10632831, compound

Participants

Reaction Steps

Compound 14 (525 mg, 1.70 mmol) was dissolved in CH2Cl2 (10 mL) and TFA (2.0 mL) was added together with a drop of water. The solution was stirred for 15 h at rt. Then aq NaHCO3 (5%, 35 mL) was added and the phases were separated. The organic phase was washed twice with aq NaHCO3 (5%), once with brine and dried (Na2SO4). The solvents were removed under reduced pressure and the oily residue was purified by column chromatography (silica, ether/hexanes, 1:2), affording a yellow oil (279 mg, 74%). IR (neat): {tilde over (v)} 3037, 2928, 2849, 2731, 1693, 1605; 1H NMR δ 1.88–1.99 (m, 2H), 2.35 (s, 3H), 2.78 (t, 3J=7.3 Hz, 2H), 2.89 (t, 3J=7.3 Hz, 2H), 7.35, 7.81 (AA′BB′, 2×2H), 9.98 (s, 1H); 13C NMR (APT) δ 28.1 (+), 30.4 (+), 34.7 (+), 128.8 (−), 129.7 (−), 134.4 (+), 148.3 (+), 191.6 (−), 195.2 (+); GC-MS (EI) obsd 222, 180, 146, 133, 117, 105, 91, 43.

Provenance & Evidence