Hexane → HCID 44138554, compound

HRID 2110616Notes

Reaction equation

HRID 2110616 reaction equation
[C:1]1([C@@H:7]2[CH2:11][O:10][C:9](=[O:12])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.CCCCCC.[Cl:24][C:25](OC(Cl)(Cl)Cl)=[O:26]>C1COCC1>[O:12]=[C:9]1[N:8]([C:25]([Cl:24])=[O:26])[C@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:11][O:10]1

Participants

6

Reactant 4

HCID 8058HexaneHCID 10426DiphosgeneHCID 730425(4R)-4-phenyl-1,3-oxazolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 44138554HCID 44138554, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (R)-(−)-4-phenyl-2-oxazolidinone in THF (200 mL) at 0° C. was slowly added a 2.5 M solution of butyllithium in hexane (19 mL, 0.03 mol). The mixture was stirred at 0° C. for 30 min and then cooled to −78° C. Trichloromethyl chloroformate (7.8 mL, 0.03 mol) was added quickly in one portion and the reaction solution was stirred at −78° C. for 30 min. The resulting mixture was allowed to warm to room temperature, and was subsequently concentrated in vacuo. The resulting residue was taken up in CH2Cl2 (200 mL) and filtered, and the filtrate was concentrated in vacuo to afford the title compound as an off-white solid (4.5 g, 65%).

Workup

  1. temperaturecooled to −78° C
  2. stirringthe reaction solution was stirred at −78° C. for 30 min
  3. temperatureto warm to room temperature
  4. concentrationwas subsequently concentrated in vacuo
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8828a17973d14b8fa91a82d0355454ac
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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