Acetic Acid → HCID 57472889, compound

Participants

Reaction Steps

To a stirred solution of 7 (5.37 g, 21.6 mmol, 1 equiv) was dissolved in THF (100 mL) and AcOH (4.99 mL, 86.5 mmol, 4 equiv) was added followed by dropwise addition of TBAF (1 M in THF; 86.5 mL, 86.5 mmol, 4 equiv). The resulting reaction was allowed to stir at room temperature for 24 h. The reaction was diluted with Et2O, washed with brine (×2), dried (MgSO4), filtered, and concentrated under reduced pressure. The crude mixture was purified by chromatography on SiO2 (EtOAc/hexanes, 1:10) to give 3.85 g (100% yield) of the desired product as a colorless oil: Rf 0.36 (EtOAc/hexanes, 1:10); IR (CDCl3) 3286, 2999, 2954, 1593, 1457, 1428, 1344, 1323, 1288, 1204, 1154, 1064, 827; 1H NMR (400 MHz, CDCl3) δ 6.53 (d, 2 H, J=2.4 Hz), 6.35 (t, 1 H, J=2.4 Hz), 3.79 (s, 6 H), 3.56 (d, 2 H, J=2.8 Hz), 2.20 (t, 1H, J=2.8 Hz); 13C NMR (100 MHz, CDCl3) δ 160.9, 138.3, 105.9, 98.7, 81.7, 70.6, 55.3, 25.0; HRMS (EI+) m/z calcd for C11H12O2 176.0837, found 176.0834.

Provenance & Evidence