Acetic Acid → HCID 69260546, compound

HRID 899023Notes

Reaction equation

HRID 899023 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[C:11]([O:22][Si:23]([CH3:27])([CH3:26])[CH2:24][CH3:25])(=[O:21])[CH2:12][C:13]([O:15][Si:16]([CH3:20])([CH3:19])[CH2:17][CH3:18])=[O:14].N1CCCCC1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[C:12]([C:11]([O:22][Si:23]([CH3:27])([CH3:26])[CH2:24][CH3:25])=[O:21])[C:13]([O:15][Si:16]([CH3:19])([CH3:20])[CH2:17][CH3:18])=[O:14])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 312444-MethoxybenzaldehydeHCID 86602709HCID 86602709, compound

Product 1

HCID 69260546HCID 69260546, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

4-Methoxybenzaldehyde (12.3 g, 0.03 mol) and di(methyltrimethylsilyl) malonate (25 g, 0.09 mol) in 40 ml of dry toluene in the presence of 0.9 ml of piperidine and 0.5 ml of acetic acid are refluxed for 4 hours in a reactor equipped with Dean-Stark apparatus. The water formed is removed azeotropically. The mixture is cooled and the toluene is removed by distillation. The reaction mixture is taken up in diisopropyl ether. The organic phase is washed 3 times with water, dried over sodium sulfate and filtered, and the solvent is evaporated off under vacuum. The solid obtained is recrystallized from isopropanol to give 25.1 g (yield: 71%) of the derivative of Example 13 in the form of a white powder:

Workup

  1. customequipped with Dean-Stark apparatus
  2. customis removed azeotropically
  3. temperatureThe mixture is cooled
  4. customthe toluene is removed by distillation
  5. washThe organic phase is washed 3 times with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent is evaporated off under vacuum
  9. customThe solid obtained
  10. customis recrystallized from isopropanol
  11. customto give 25.1 g (yield: 71%) of the derivative of Example 13 in the form of a white powder

Sources & evidence

ORD record
ord-08b645717d31475690425848d89f0880
Source dataset
uspto-grants-2008_04
Patent number
US07354571B2

Reaction notes

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