Acetic Acid → HCID 70224837, compound

HRID 1532744Notes

Reaction equation

HRID 1532744 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1C=O.[C:24](O)(=O)C.N1CCCCC1.[C:34]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])(=[O:40])[CH2:35][C:36]([O:38][CH3:39])=[O:37]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[CH:20][C:21]([CH:24]=[C:35]([C:36]([O:38][CH3:39])=[O:37])[C:34]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 2733872tert-Butyl methyl malonateHCID 22070305HCID 22070305, compound

Product 1

HCID 70224837HCID 70224837, compoundYield 179.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of [(5-methyl-2-phenyloxazol-4-yl) ethoxy] benzaldehyde (4.0 g, 13.1 mmol) in toluene were added acetic acid (0.41 ml, 6.5 mmol), piperidine (0.64 ml, 6.5 mmol) and tert-butyl methyl malonate (2.8 ml, 15.6 mmol). While removing water through Dean-Stark trap, the mixture was refluxed under heating for 1.5 hr. After completion of the reaction, toluene (30 ml) was added and the mixture was washed with water (20 ml×3) and saturated brine (50 ml), dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (developing solvent; n-hexane:ethyl acetate=75:25) to give the title compound (5.4 g, yield 89%, 1:1 geometric isomer mixture) as a pale yellow oil.

Workup

  1. customWhile removing water through Dean-Stark trap
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for 1.5 hr
  4. customAfter completion of the reaction, toluene (30 ml)
  5. additionwas added
  6. washthe mixture was washed with water (20 ml×3) and saturated brine (50 ml)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by silica gel column chromatography (developing solvent; n-hexane:ethyl acetate=75:25)

Sources & evidence

ORD record
ord-8361c8f45835488babdcd2c52d6a7f87
Source dataset
uspto-grants-2001_03
Patent number
US06204277B1

Reaction notes

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