Ethyl Acetoacetate → HCID 86715644, compound

HRID 926486Notes

Reaction equation

HRID 926486 reaction equation
[H-].[Na+].[O:3]=[C:4]([CH3:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[F:12][C:13]([F:23])([F:22])[C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1>C(COC)OC>[O:3]=[C:4]([CH3:11])[CH:5]([CH2:18][C:17]1[CH:16]=[CH:15][C:14]([C:13]([F:12])([F:22])[F:23])=[CH:21][CH:20]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 24758Sodium hydrideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzene

Product 1

HCID 86715644HCID 86715644, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Sodium hydride (60% dispersion in mineral oil, 1.5 g, 38.4 mmol) was added in portions over 2 minutes to an ice-cooled, stirring solution of ethyl 3-oxobutanoate (5 g, 38.4 mmol) in dry dimethoxyethane (65 mL). After 30 minutes, a solution of 4-(trifluoromethyl)benzyl bromide (9.2 g, 38.4 mmol) in dry dimethoxyethane (10 mL) was added dropwise over 2 minutes. The flask was removed from the cooling bath. After 2 hours, water (10 mL) was added. The mixture was partitioned between half-saturated aqueous sodium chloride solution (50 mL) and ethyl acetate (150 mL). The layers were separated. The organic layer was dried with magnesium sulfate and the dried solution was filtered. The filtrate was concentrated and the residue was purified by flash-column chromatography on silica gel eluting with hexanes-ethyl acetate to provide the title compound as a colorless liquid.

Workup

  1. temperaturecooled
  2. customThe flask was removed from the cooling bath
  3. waitAfter 2 hours
  4. additionwater (10 mL) was added
  5. customThe mixture was partitioned between half-saturated aqueous sodium chloride solution (50 mL) and ethyl acetate (150 mL)
  6. customThe layers were separated
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationthe dried solution was filtered
  9. concentrationThe filtrate was concentrated
  10. customthe residue was purified by flash-column chromatography on silica gel eluting with hexanes-ethyl acetate

Sources & evidence

ORD record
ord-a86e7e059d7a418aaf1747d85ee790a0
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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