Sodium Chloride → 5-(1-Methyl-1-phenylethyl)oxazole

Temperature

-78 °C

To a solution of methyl isocyanide (1.3 mmol, 1.3 eq.) in THF (5 mL) at −78° C. was added dropwise a solution of n-BuLi in Hexane (2.5 M, 1.3 mmol, 1.3 eq.). The resulting yellowish solution was stirred at −78° C. for an additional 45 min and 2-Methyl-2-phenylpropionyl chloride (1.0 mmol, 1.0 eq.) was slowly added. The mixture was stirred at −78° C. for an additional 1 h and allowed to warm to room temperature followed by the addition of saturated aqueous NaCl solution (5 mL). The mixture was extracted by EtOAc (3×5 mL) and the combined organic extracts were washed by saturated aqueous NaCl solution, dried by Na2SO4, filtered and evaporated in vacuo. The residue was further purified by flash chromatography (silica gel, 10% EtOAc/Hexanes) to afford 5-(1-Methyl-1-phenylethyl)oxazole as a colorless oil (101 mg, 54%). 1H NMR: δ (400 MHz, CDCl3) 7.74 (s,1H), 7.30 (m, 2H), 7.23 (m, 3H), 6.85 (s,1H), 1.69 (s, 6H). MS (M+H+): 188.1

1. stirringThe mixture was stirred at −78° C. for an additional 1 h
2. temperatureto warm to room temperature
3. extractionThe mixture was extracted by EtOAc (3×5 mL)
4. washthe combined organic extracts were washed by saturated aqueous NaCl solution
5. dry with materialdried by Na2SO4
6. filtrationfiltered
7. customevaporated in vacuo
8. customThe residue was further purified by flash chromatography (silica gel, 10% EtOAc/Hexanes)

ORD record

ord-8c9440dcf2664164a7a89d723deae290

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07420055B2