Sodium Hydroxide → HCID 71279140, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-phenyl-5-(pyridin-3-yl)oxazole-4-carboxylate (1.33 g, 4.75 mmol) in THF (25 mL) was added dropwise at 0-5° C. lithium aluminum hydride (1M solution in THF, 4.75 mL, 4.75 mmol) over a period of 15 min. The reaction mixture was stirred at 0-5° C. for 1 h. Water (20 mL) was added dropwise over a period of 10 min. The reaction mixture was poured into KHSO4 (10% aqueous solution, 75 mL) and extracted with ethyl acetate (2×100 mL). The organic phase was washed with water (2×50 mL) and brine (1×50 mL), dried over MgSO4 and concentrated in vacuo to give 490 mg crude product. The combined aqueous phases were adjusted to pH 8 with NaOH (1M solution) and extracted with dichloromethane (3×100 mL). The dichloromethane phase was dried over MgSO4, filtered and evaporated to give 480 mg brown foam. The product was obtained after purification of the combined crude products by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as light brown solid (210 mg, 832 μmol, 17.5%).

Provenance & Evidence