Sodium hydride → HCID 66718591, compound

Participants

Reaction Steps

To a stirred suspension of sodium hydride (75 mg, 3.1 mmol) in anhydrous 1,2-dimethoxyethane (30 mL) was added a solution of 3-(benzyloxy)-2-(2-chloro-6-(trifluoromethyl)pyridine-3-yloxy)propan-1-ol (1.13 g, 3.1 mmol) in anhydrous 1,2-dimethoxyethane (30 mL), dropwise over 5 minutes. The reaction was heated at reflux for 90 minutes, then allowed to cool. The reaction mixture was poured into saturated NaHCO3 solution (50 mL) and extracted with EtOAc (3×30 mL). The combined organics were washed with brine (3×30 mL), dried (MgSO4), filtered and concentrated. Flash chromatography (0 to 20% EtOAc in hexanes) gave the title compound (450 mg, 43%) as an oil. m/z=325.6 (M+1), r.t.=3.46 mins. 1H NMR (400 MHz; CDCl3) 57.36-7.25 (7H, m), 4.62 (2H, d), 4.60-4.53 (1H, m, 4.43 (1H, dd), 4.18 (1H, dd), 3.87 (1H, dd), 3.74 (1H, dd).

Provenance & Evidence