Hexane → HCID 11010755, compound

HRID 1761365Notes

Reaction equation

HRID 1761365 reaction equation
CC([N:4]1[CH2:8][CH2:7][O:6][C:5]1=[O:9])C.[CH2:10]([Li])[CH2:11][CH2:12]C.CCCCCC.[C:21]1([CH2:27][CH2:28][C:29](Cl)=[O:30])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1>[C:21]1([CH2:27][CH2:28][C:29]([N:4]2[C@H:8]([CH:11]([CH3:12])[CH3:10])[CH2:7][O:6][C:5]2=[O:9])=[O:30])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 64801Benzenepropanoyl chlorideHCID 2371943-isopropyl-1,3-oxazolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 11010755HCID 11010755, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 4 (2-propyl)-oxazo-lidine-2-one in anhydrous tetrahydrofuran (250 mL) under a nitrogen atmosphere at -78° C. were added in a dropwise fashion a solution of 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 at the temperature. 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%). mp =86.5 to 87.5° C. Mass spectrum: (M+NH4)+ =279, (M+H)+=262. Mass spectrum: (M+NH4)

Workup

  1. temperatureThe reaction was warmed to room temperature
  2. stirringstirred 1 to 2 h at the temperature
  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

Sources & evidence

ORD record
ord-3aafd3891f8f45a09a21f8f4d806c63b
Source dataset
uspto-grants-1989_05
Patent number
US04826815

Reaction notes

Loading…