2-Methoxybenzaldehyde → Ethyl 2-azido-3-(2-methoxyphenyl)propenoate

HRID 2185676Notes

Reaction equation

HRID 2185676 reaction equation
[Na].[CH3:2][O:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O.[N:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N+:13]=[N-:14]>C(O)C>[N:12]([C:15](=[CH:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[O:3][CH3:2])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N+:13]=[N-:14]

Participants

5

Reactant 3

HCID 86582-MethoxybenzaldehydeHCID 69480Acetic acid, azido-, ethyl esterHCID 5360545Sodium

Product 1

HCID 72978722Ethyl 2-azido-3-(2-methoxyphenyl)propenoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-18 °C

Procedure

Pieces of sodium (3.678 g, 160 mmol) were added portionwise to ethanol (200 ml) over a period of 30 minutes. The resulting solution was cooled to −18° C. and a mixture of 2-methoxybenzaldehyde (4.832 g, 40 mmol) and ethyl azidoacetate (160 mmol) were then added over a period of one hour at a rate which allowed the temperature to be maintained below −15° C. After 3 hours, the solution was stored at 5° C. for 2 days in order to give a crystalline product which was collected by filtration and washed with cold hexane.

Workup

  1. additionwere then added over a period of one hour at a rate which
  2. temperatureto be maintained below −15° C
  3. waitthe solution was stored at 5° C. for 2 days in order
  4. customto give a crystalline product which
  5. filtrationwas collected by filtration
  6. washwashed with cold hexane

Sources & evidence

ORD record
ord-ec3388e449c545979894da0f39e602b3
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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