Hexane → HCID 11010755, compound

Temperature

-78 °C

To a stirred solution of 4-(2-propyl)-oxazolidine-2-one in anhydrous tetrahydrofuran (250 ml under a nitrogen atmosphere at -78° C. were added in a dropwise fashion a solution of n-butyllithium in hexane (50 ml, 77.4 mmol) over 5 to 10 min. After stirring an additional 20 min at -78° C. 3-phenylpropionyl chloride (12.7 ml, 85.2 mmol) was added neat. The reaction was warmed to room temperature and stirred 1 to 2 h. The reaction was quenched by adding 100 ml of saturated aqueous ammonium chloride and the volatiles removed by rotary evaporation. The resulting aqueous residue was extracted three times with ether and the combined organic phases were washed with brine, dried (Na2SO4, filtered and concentrated in vacuo. Recrystallization from hexanes/ethyl acetate provided the title compound (16.6 g, 82%). m.p.=86.5 to 87.5° C. Mass spectrum: (M+NH4)+ =279, (M+H)+ = 262.

1. temperatureThe reaction was warmed to room temperature
2. stirringstirred 1 to 2 h
3. customThe reaction was quenched
4. additionby adding 100 ml of saturated aqueous ammonium chloride
5. customthe volatiles removed by rotary evaporation
6. extractionThe resulting aqueous residue was extracted three times with ether
7. washthe combined organic phases were washed with brine
8. dry with materialdried (Na2SO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customRecrystallization from hexanes/ethyl acetate

ORD record

ord-63a504f21f954f4981e611450c52e1e1

Source dataset

uspto-grants-1991_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05059589