Dimethylformamide → Methyl 4-methoxy-3-(1-methyl-2-oxobutoxy)benzoate

HRID 1057928Notes

Reaction equation

HRID 1057928 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][C:4]=1[OH:13].Br[CH:15]([C:17](=[O:20])[CH2:18][CH3:19])[CH3:16].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][C:4]=1[O:13][CH:15]([CH3:16])[C:17](=[O:20])[CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5450922-Bromo-3-pentanoneHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 22734323Methyl 4-methoxy-3-(1-methyl-2-oxobutoxy)benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of methyl 3-hydroxy-4-methoxy benzoate (19.3 g), 2-bromo-3-pentanone (19.2 ml), potassium carbonate (29.3 g), and DMF (193 ml) was stirred at 90° C. for 2 hours. After being allowed to stand for cooling, water was added to the mixture followed by extraction with toluene. The organic layer was washed with a saturated saline and dried over sodium sulfate, and the solvent was distilled off. The residue was purified by column chromatography (silica gel, hexane:ethyl acetate=3:1) to give Compound IIk-a (25.8 g, 91.5%) as a colorless oily substance.

Workup

  1. temperaturefor cooling
  2. extractionfollowed by extraction with toluene
  3. washThe organic layer was washed with a saturated saline
  4. dry with materialdried over sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by column chromatography (silica gel, hexane:ethyl acetate=3:1)
  7. customto give Compound IIk-a (25.8 g, 91.5%) as a colorless oily substance

Sources & evidence

ORD record
ord-bf5cae24d16a45cb90fda3d12b56eda7
Source dataset
uspto-grants-2003_02
Patent number
US06514996B2

Reaction notes

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