Hexane → HCID 21187685, compound

HRID 1637087Notes

Reaction equation

HRID 1637087 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:13]([CH:14]3[CH2:16][CH2:15]3)[O:12][C:11](=[O:17])[NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8].C([Li])CCC.CCCCCC.[CH:29]1[C:34]([N+:35]([O-:37])=[O:36])=[CH:33][CH:32]=[C:31]([Cl-]C([O-])=O)[CH:30]=1.[C:42](=O)([OH:44])[O-:43].[Na+]>C1COCC1>[N+:35]([C:34]1[CH:29]=[CH:30][C:31]([O:44][C:42]([N:10]2[CH:9]([C:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=3)[CH:13]([CH:14]3[CH2:15][CH2:16]3)[O:12][C:11]2=[O:17])=[O:43])=[CH:32][CH:33]=1)([O-:37])=[O:36]

Participants

6

Reactant 4

HCID 8058HexaneHCID 516892Sodium BicarbonateHCID 22993473HCID 22993473, compoundHCID 178418339Butyllithium

Product 1

HCID 21187685HCID 21187685, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-(3,4-difluorophenyl)-5-cyclopropyl-oxazolidin-2-one (2 g, 8.3 mmol) in 100 mL THF was added a solution of n-butyllithium in hexane (9.1 mmol) dropwise via a syringe under an argon atmosphere at -78° C. The resulting yellow solution was stirred at -78° C. for 10 min. To this solution was then added dropwise via syringe 4-nitrophenylchloroformate (1.03 g, 5.1 mmol) in 20 mL of THF. The reaction was stirred at -78° for 10 min. The reaction mixture was poured into saturated sodium bicarbonate and extracted with ethyl acetate (2×200 mL). The organic extracts were washed with brine, and the organic layer was dried over Na2SO4. The solvent was removed after filtration, and the residue was purified by column chromatography on silica gel 30% ethyl acetate hexane. The material was rechromatographed on silica gel eluting with 2% acetone/methylene chloride to give 1.2 g the product as a thick syrup which solidified upon standing.

Workup

  1. stirringThe reaction was stirred at -78° for 10 min
  2. extractionextracted with ethyl acetate (2×200 mL)
  3. washThe organic extracts were washed with brine
  4. dry with materialthe organic layer was dried over Na2SO4
  5. customThe solvent was removed
  6. filtrationafter filtration
  7. customthe residue was purified by column chromatography on silica gel 30% ethyl acetate hexane
  8. customThe material was rechromatographed on silica gel eluting with 2% acetone/methylene chloride

Sources & evidence

ORD record
ord-0a5522bfa1a44e84a1b02ae520537ea6
Source dataset
uspto-grants-2000_03
Patent number
US06037354

Reaction notes

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