Sodium Hydroxide → HCID 58355252, compound

HRID 1184228Notes

Reaction equation

HRID 1184228 reaction equation
[CH2:1]([O:8][CH2:9][C:10](=O)[CH2:11][C:12]([O:14]C)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[N+:18]=[N-:19].C[O-].[Na+].[OH-].[Na+]>CO>[CH2:1]([O:8][CH2:9][C:10]1[N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:18]=[N:19][C:11]=1[C:12]([OH:14])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 69319AzidobenzeneHCID 10942334Sodium MethoxideHCID 12768799Methyl 4-(benzyloxy)-3-oxobutanoate

Product 1

HCID 58355252HCID 58355252, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-(benzyloxy)-3-oxobutanoate (5.00 g) and azidobenzene (2.68 g) were dissolved in methanol (30 ml), sodium methanolate (28% methanol solution, 6.5 g) was added and the mixture was stirred at room temperature for 2 hr, and then heated under reflux for 18 hr. 1M Aqueous sodium hydroxide solution (10 ml) was added and the mixture was heated under reflux for 2 hr. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in water and washed with ethyl acetate-hexane (1:1, v/v). The obtained aqueous solution was acidified with 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (6.03 g).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 hr
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 2 hr
  5. temperatureThe reaction mixture was cooled to room temperature
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in water
  8. washwashed with ethyl acetate-hexane (1:1
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe extract was washed with saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1c8ca308df7840048428894e72545a12
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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