Ammonium Chloride → Ethyl 3-(4-benzyloxy-2-chlorophenyl)-2-azidopropenoate

HRID 564982Notes

Reaction equation

HRID 564982 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[C:11]([Cl:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([OH:21])(=[O:20])[CH3:19].C([N:24]=[N+:25]=[N-:26])C.[O-][CH2:28][CH3:29].[Na+].[Cl-].[NH4+]>C(O)C>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[C:19]([N:24]=[N+:25]=[N-:26])[C:18]([O:21][CH2:28][CH3:29])=[O:20])=[C:11]([Cl:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2723922Sodium ethoxideHCID 140340774-(Benzyloxy)-2-chlorobenzaldehydeHCID 86756206HCID 86756206, compound

Product 1

HCID 53783165Ethyl 3-(4-benzyloxy-2-chlorophenyl)-2-azidopropenoateYield 57.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
-10 °C

Procedure

An ethanol solution, 70 ml, containing 5.40 g (21.9 mmol) of 4-benzyloxy-2-chlorobenzaldehyde and 11.3 g (87.6 mmol) of ethyl azide acetate was gradually added dropwise to 70 ml of an ethanol solution of 5.95 g (87.6 mmol) of sodium ethoxide at −10° C. After stirring at −10° C. for further 5 hours, the reaction temperature was slowly elevated to room temperature. The reaction mixture was poured onto 200 ml of saturated ammonium chloride aqueous solution and the mixture was extracted three times with ethyl acetate. The combined extracts were then washed with saturated ammonium chloride solution and next with saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 4.50 g (57.5%) of ethyl 3-(4-benzyloxy-2-chlorophenyl)-2-azidopropenoate.

Workup

  1. customwas slowly elevated to room temperature
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. washThe combined extracts were then washed with saturated ammonium chloride solution and next with saturated sodium chloride solution
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b3ea862860d84752a5790b0c1a26c079
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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