Acetic Acid → HCID 69260667, compound

HRID 899022Notes

Reaction equation

HRID 899022 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.[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][CH:8]=[CH:7][C:4]=1[CH:5]=[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]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 86582-MethoxybenzaldehydeHCID 86602709HCID 86602709, compound

Product 1

HCID 69260667HCID 69260667, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2-Methoxybenzaldehyde (0.98 g, 7.2×10−3 mol) and di(methyltrimethylsilyl) malonate (2 g, 7.23×10−3 mol) in 8 ml of dry toluene in the presence of 6 mg of piperidine and 5 mg of acetic acid are refluxed for 5 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 twice with water, dried over sodium sulfate and filtered, and the solvent is evaporated off under vacuum. The brown oil obtained is purified by chromatography on a column of silica (eluent: 95/5 heptane/EtOAc). 2.1 g of clean fractions (yield: 74%) of the derivative of Example 12 are recovered in the form of a colorless viscous oil:

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 twice with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent is evaporated off under vacuum
  9. customThe brown oil obtained
  10. customis purified by chromatography on a column of silica (eluent: 95/5 heptane/EtOAc)
  11. custom2.1 g of clean fractions (yield: 74%) of the derivative of Example 12 are recovered in the form of a colorless viscous oil

Sources & evidence

ORD record
ord-02e0f037a54c49ce8326ed260a26dbf7
Source dataset
uspto-grants-2008_04
Patent number
US07354571B2

Reaction notes

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