Sodium hydride → HCID 86602758, compound

Participants

Reaction Steps

2-Methyl-2-phenylpropane-1,3-diol (3.37 g, 20.3 mmol) was dissolved in DMF, NaH (812 mg, 60%, 20.3 mmol) was added and the mixture was stirred at room temperature for 30 minutes. A DMF solution of 3,5-bistrifluoromethylbenzyl bromide (6.23 g, 20.3 mmol) was added in one portion and stirred for another 1 hour before it was quenched with water and extracted with ethyl acetate. The organic phase was washed with brine and dried with Na2SO4 before being concentrated. The crude product was purified by silica flash chromatography using 15% ethyl acetate in hexanes to yield 4.2 grams (52.8%) of the desired mono-alkylated product. 1H NMR (500 MHz, CDCl3) δ: 1.40 (s, 3 H) 1.78 (s, 1 H) 3.72 (d, J=9.16 Hz, 1 H) 3.82 (d, J=9.16 Hz, 1 H) 3.89 (m, 2 H) 4.64 (s, 2 H) 7.26 (m, 1 H) 7.37 (m, 4 H) 7.72 (s, 2 H) 7.79 (s, 1 H).

Provenance & Evidence