Diketene → HCID 14099895, compound

HRID 569169Notes

Reaction equation

HRID 569169 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]=[CH:15]/[CH2:16][O:17][CH2:18][CH2:19][OH:20])=[CH:10][CH:9]=2)[CH:2]=1.[CH2:21]=[C:22]1[O:26][C:24](=[O:25])[CH2:23]1>O1CCCC1.C(N(CC)CC)C>[C:24]([O:20][CH2:19][CH2:18][O:17][CH2:16]/[CH:15]=[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:25])[CH2:23][C:22]([CH3:21])=[O:26]

Participants

5

Reactant 2

HCID 12661DiketeneHCID 13745526HCID 13745526, compound

Product 1

HCID 14099895HCID 14099895, compoundYield 72.2%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

In 50 ml of tetrahydrofuran was dissolved 5.4 g of 2-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]allyloxy]ethanol, and one drop of triethylamine was added to the resulting solution. To this solution was dropwise added a mixture of 1.8 g of diketene and 4 ml of tetrahydrofuran under reflux over one hour, and then the resulting mixture was subjected to reaction at the same temperature for a further 30 minutes. Subsequently, the solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a column chromatography [Wako Silica Gel C-200, eluant: benzene:ethyl acetate (2:1 by volume)] to obtain 5.1 g (yield 72.2%) of oily 2-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]allyloxy]ethyl acetoacetate.

Workup

  1. additionwas added to the resulting solution
  2. additionTo this solution was dropwise added
  3. temperatureunder reflux over one hour
  4. customthe resulting mixture was subjected to reaction at the same temperature for a further 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 [Wako Silica Gel C-200, eluant: benzene:ethyl acetate (2:1 by volume)]

Sources & evidence

ORD record
ord-6887bc6e7c034735abc6529f1be81238
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

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