Ethyl Acetoacetate → HCID 89767759, compound

HRID 591524Notes

Reaction equation

HRID 591524 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].Br[CH2:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16]>C1COCC1.[Cl-].[Na+].O>[C:3]([CH:2]([CH2:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])[C:1]([O:7][CH2:8][CH3:9])=[O:6])(=[O:4])[CH3:5]

Participants

6

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 24758Sodium hydrideHCID 790083-Bromo-1,1,1-trifluoro-2-propanone

Product 1

HCID 89767759HCID 89767759, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of ethyl acetoacetate (3.98 mL) in THF (dry) (50 mL) was added NaH (1.571 g) at 0° C., and the mixture was stirred for 30 min at the same temperature. To the mixture was added 3-bromo-1,1,1-trifluoroacetone (5 g) 0° C., and the mixture was stirred for 3 h. The mixture was poured into brine at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (1.570 g).

Workup

  1. stirringthe mixture was stirred for 3 h
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed successively with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-626235c5910f4b0a9b788bcabbf70c27
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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