Pyridine → HCID 86602759, compound

Participants

Reaction Conditions

Reaction Steps

3-(3,5-bis(trifluoromethyl)benzyloxy)-2-methyl-2-phenylpropan-1-ol (1.72 g, 4.39 mmol) was mixed with pyridine (1.39 g, 17.6 mmol) in anhydrous methylene chloride (20 ml) and cooled to −20° C. Solid p-toluenesulfonyl chloride (3.35 g, 17.6 mmol) was added in one portion and the mixture was warmed up naturally to room temperature and stirred overnight. The mixture was then loaded directly onto silica column and eluted with 5% ethyl aceta in hexanes. 1.89 g (79%) of the desired product was obtained. 1H NMR (500 MHz, CDCl3) δ: 1.37 (s, 3 H) 2.38 (s, 3 H) 3.66 (d, J=2.75 Hz, 2 H) 4.21 (d, J=9.46 Hz, 1 H) 4.27 (d, J=9.46 Hz, 1 H) 4.52 (s, 2 H) 7.27 (m, 5 H) 7.35 (d, J=8.24 Hz, 2 H) 7.62 (s, 2 H) 7.70 (s, 1 H) 7.80 (d, J=8.24 Hz, 2 H).

Provenance & Evidence