Ethyl Acetoacetate → HCID 90386888, compound

HRID 2170218Notes

Reaction equation

HRID 2170218 reaction equation
[H-].[Na+].[O:3]=[C:4]([CH3:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:15]>O1CCCC1>[C:4]([CH:5]([CH2:13][C:14](=[O:15])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:11]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 24758Sodium hydrideHCID 130740462-Bromo-1-(2-phenoxyphenyl)ethan-1-one

Product 1

HCID 90386888HCID 90386888, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of sodium hydride (60% oil dispersion, 0.157 g, 3.92 mmol) and tetrahydrofuran (6.1 mL) was cooled to 0° C., treated dropwise with ethyl 3-oxobutanoate (0.413 mL, 3.27 mmol) and stirred at 0° C. for 30 minutes. A solution of 2-bromo-1-(2-phenoxyphenyl)ethanone (1.05 g, 3.6 mmol) in tetrahydrofuran (2 mL) was added dropwise and stirring was continued for 5.5 hours. The reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution and washed with saturated aqueous sodium chloride. The combined aqueous layers were extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (silica gel, 2-20% ethyl acetate in hexanes) to give 1.1 g (100%) of the title compound.

Workup

  1. stirringstirring
  2. waitwas continued for 5.5 hours
  3. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution
  4. washwashed with saturated aqueous sodium chloride
  5. extractionThe combined aqueous layers were extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (silica gel, 2-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b86ab3aef3524b218422c8725519ab11
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

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