Methyl acetoacetate → 3-Oxo-2-[2-oxo-2-(2-trifluoromethoxy-phenyl)-ethyl]-butyric acid methyl ester

HRID 229859Notes

Reaction equation

HRID 229859 reaction equation
[CH3:1][O:2][C:3](=[O:8])[CH2:4][C:5](=[O:7])[CH3:6].C[O-].[Na+].Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][C:23]([F:26])([F:25])[F:24])=[O:15]>C1COCC1>[CH3:1][O:2][C:3](=[O:8])[CH:4]([CH2:13][C:14](=[O:15])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][C:23]([F:24])([F:25])[F:26])[C:5](=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 27786842-(Trifluoromethoxy)phenacyl bromideHCID 10942334Sodium Methoxide

Product 1

HCID 690212293-Oxo-2-[2-oxo-2-(2-trifluoromethoxy-phenyl)-ethyl]-butyric acid methyl esterYield 71.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2.6 g of 3-oxo-butyric acid methyl ester in THF (50 ml) and 4.6 ml of a solution of sodium methoxide (5.4 M in methanol) was added over 15 minutes a solution of 6.7 g of 2-bromo-1-[2-(trifluoromethoxy)phenyl]-ethanone in 30 ml of THF. The reaction mixture was allowed to stir at room temperature for 17 hours. The solvent was removed, the residue was diluted in diethyl ether and washed several times with water. The organic phase was dried with sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel; heptane/ethyl acetate) to give 5.1 g of the title compound. MS (EI) 319.1 (M+H)+.

Workup

  1. customThe solvent was removed
  2. additionthe residue was diluted in diethyl ether
  3. washwashed several times with water
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel; heptane/ethyl acetate)

Sources & evidence

ORD record
ord-11cff4c3eb7340818ece68846ae3caec
Source dataset
uspto-grants-2009_07
Patent number
US07563910B2

Reaction notes

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