Diketene → HCID 14010660, compound

HRID 569182Notes

Reaction equation

HRID 569182 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[C:15](\[CH3:24])/[CH2:16][O:17][CH2:18][C:19]([CH3:23])([CH3:22])[CH2:20][OH:21])=[CH:10][CH:9]=2)[CH:2]=1.[CH2:25]=[C:26]1[O:30][C:28](=[O:29])[CH2:27]1>C(OCC)(=O)C.C(N(CC)CC)C>[C:28]([O:21][CH2:20][C:19]([CH3:23])([CH3:22])[CH2:18][O:17][CH2:16]/[C:15](/[CH3:24])=[CH:14]/[C:11]1[CH:12]=[CH:13][C:8]([CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:9][CH:10]=1)(=[O:29])[CH2:27][C:26]([CH3:25])=[O:30]

Participants

5

Reactant 2

HCID 12661DiketeneHCID 14010659HCID 14010659, compound

Product 1

HCID 14010660HCID 14010660, compoundYield 60.9%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

In 50 ml of ethyl acetate was dissolved 9.2 g of 3-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyloxy]-2,2-dimethylpropanol, and one drop of triethylamine was added to the resulting solution. To the solution was added dropwise a mixture of 3.1 g of diketene and 9.2 ml of ethyl acetate under reflux over one hour, and the resulting mixture was then subjected to reaction at the same temperature for 30 minutes. Subsequently, the solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a column chromatography [Merck Silica Gel, 70-230 mesh, eluant: toluene:ethyl acetate (4:1 by volume)] to obtain 7.05 g (yield 60.8%) of oily 3-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyloxy]-2,2-dimethylpropyl acetoacetate.

Workup

  1. additionwas added to the resulting solution
  2. additionTo the solution was added dropwise
  3. temperatureunder reflux over one hour
  4. customthe resulting mixture was then subjected to reaction at the same temperature for 30 minutes
  5. customSubsequently, the solvent was removed by distillation under reduced pressure
  6. customthe residue thus obtained
  7. customwas purified by a column chromatography [Merck Silica Gel, 70-230 mesh, eluant: toluene:ethyl acetate (4:1 by volume)]

Sources & evidence

ORD record
ord-ec4664891e6c402da1a619f15211ad0f
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

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