Methyl acetoacetate → HCID 68842837, compound

HRID 2105767Notes

Reaction equation

HRID 2105767 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]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[O:24][CH3:25])=[O:15]>C1COCC1>[CH3:1][O:2][C:3](=[O:8])[CH:4]([CH2:13][C:14]([C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[O:24][CH3:25])=[O:15])[C:5](=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 709972-Bromo-2',5'-dimethoxyacetophenoneHCID 10942334Sodium Methoxide

Product 1

HCID 68842837HCID 68842837, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3 g of 3-oxo-butyric acid methyl ester in THF (60 ml) and 5.2 ml of a solution of sodium methoxide (5.4 M in methanol) was added over 15 minutes a solution of 7 g of 2-bromo-1-(2,5-dimethoxy-phenyl)-ethanone in 30 ml of THF. The reaction mixture was allowed to stir at room temperature for 16 hours, during which time a precipitation occurred. The reaction mixture was then diluted in diethyl ether and washed several times with water. The organic phase was then dried with sodium sulfate and concentrated in vacuo. The residue was then triturated with isopropyl ether and filtered to give 6.3 g of the title compound. MS (ISP) 295.1 (M+H)+.

Workup

  1. customa precipitation
  2. additionThe reaction mixture was then diluted in diethyl ether
  3. washwashed several times with water
  4. dry with materialThe organic phase was then dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was then triturated with isopropyl ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-4c9d8853b18243f580a536251d0cdd07
Source dataset
uspto-grants-2009_08
Patent number
US07579369B2

Reaction notes

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