Ethyl diazoacetate → HCID 20148651, compound

HRID 569148Notes

Reaction equation

HRID 569148 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=2)[CH:2]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[N+](=[CH:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[N-].[OH-].[Na+]>C(Cl)Cl.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][O:16][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:12][CH:13]=2)[CH:2]=1

Participants

7

Reactant 4

HCID 12192Ethyl diazoacetateHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 201486224-(3-Pyridinylmethyl)benzeneethanol

Product 1

HCID 20148651HCID 20148651, compoundYield 15.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

In 10 ml of methylene chloride was dissolved 1.0 g of 2-[4-(pyridin-3-ylmethyl)phenyl]ethanol, and 980 mg of p-toluene sulfonic acid monohydrate was added thereto with ice-cooling. To the resulting solution was added 2.7 g of ethyl diazoacetate with ice-cooling, after which 700 mg of boron trifluoridediethyl ether complex was dropped into the solution. The resulting mixture was subjected to reaction at the same temperature for one hour. Subsequently, 20 ml of water and 20 ml of methylene chloride were added to the reaction mixture, and the pH thereof was adjusted to 8 with 1N aqueous sodium hydroxide solution, after which the organic layer was separated, washed successively with 20 ml of water and 20 ml of a saturated aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure. The residue thus obtained was purified by a column chromatography [Wako Silica Gel C-200, eluant: toluene:ethyl acetate (1:1 by volume)], to obtain 220 mg (yield 15.7%) of oily ethyl 2-[4-(pyridin-3-ylmethyl)phenyl]ethyloxyacetate.

Workup

  1. additionwas added
  2. temperaturewith ice-cooling
  3. temperaturecooling
  4. additionafter which 700 mg of boron trifluoridediethyl ether complex was dropped into the solution
  5. customThe resulting mixture was subjected to reaction at the same temperature for one hour
  6. customafter which the organic layer was separated
  7. washwashed successively with 20 ml of water and 20 ml of a saturated aqueous sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was then removed by distillation under reduced pressure
  10. customThe residue thus obtained
  11. customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: toluene:ethyl acetate (1:1 by volume)]

Sources & evidence

ORD record
ord-76848654a5094a93817ffea52ac8220c
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

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