Benzaldehyde, 4-(phenylmethoxy)- → Methyl 4-benzyloxy-alpha-azidocinnamate

HRID 361861Notes

Reaction equation

HRID 361861 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[N+:18]=[N-:19].C[O-].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[C:20]([N:17]=[N+:18]=[N-:19])[C:21]([O:23][CH3:24])=[O:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 4020482Methyl 2-azidoacetateHCID 10942334Sodium Methoxide

Product 1

HCID 54271879Methyl 4-benzyloxy-alpha-azidocinnamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Benzyloxybenzaldehyde (10.0 g) and methyl azidoacetate (21.7 g) are dissolved in 157 ml of methanol and cooled to -10° (ice-acetone bath). Then sodium methoxide (43.1 ml, 25% in methanol) is added dropwise such that the reaction temperature does not rise above -5°. After 2 hr, the cooling bath is removed and the reaction is warmed to 20°-25°. When no starting material remains by TLC, the reaction is diluted with ether and washed with saturated aqueous ammonium chloride. The organic layer is washed with water, saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by flash column chromatography (hexane to 5% ethyl acetate/hexane) gives the title compound.

Workup

  1. customdoes not rise above -5°
  2. customthe cooling bath is removed
  3. temperaturethe reaction is warmed to 20°-25°
  4. additionthe reaction is diluted with ether
  5. washwashed with saturated aqueous ammonium chloride
  6. washThe organic layer is washed with water, saline
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customPurification by flash column chromatography (hexane to 5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b2d35750dac440d2a14eb940a8644fcd
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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