Sodium Hydroxide → HCID 71279140, compound

Temperature

2.5 °C

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%).

1. extractionextracted with ethyl acetate (2×100 mL)
2. washThe organic phase was washed with water (2×50 mL) and brine (1×50 mL)
3. dry with materialdried over MgSO4
4. concentrationconcentrated in vacuo
5. customto give 490 mg crude product
6. extractionextracted with dichloromethane (3×100 mL)
7. dry with materialThe dichloromethane phase was dried over MgSO4
8. filtrationfiltered
9. customevaporated

ORD record

ord-b02a36e208cc4f2c8600444dbe247b17

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772510B2