3,4,5-Trimethoxybenzaldehyde → 2-Propenoic acid, 2-azido-3-(3,4,5-trimethoxyphenyl)-, methyl ester

HRID 720326

Reaction equation

HRID 720326 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=O.[N:15]([CH2:18][C:19]([O:21][CH3:22])=[O:20])=[N+:16]=[N-:17].[Na]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:18]([N:15]=[N+:16]=[N-:17])[C:19]([O:21][CH3:22])=[O:20])[CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 4020482Methyl 2-azidoacetateHCID 5360545Sodium

Product 1

HCID 43062472-Propenoic acid, 2-azido-3-(3,4,5-trimethoxyphenyl)-, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3,4,5-Trimethoxybenzaldehyde (992 mg) and methyl azidoacetate (2.91 g) were dissolved in dry methanol (2 mL), and a dry methanol solution (10 mL) of sodium (582 mg) was added dropwise to the solution at 0° C. over 2 hours under an argon atmosphere. After stirring the reaction mixture for 30 minutes as it is, it was concentrated under reduced pressure, and water was added to the residue to collect crystals deposited by filtration. The crystals were washed with water and dried to obtain the title compound.

Workup

  1. concentrationit was concentrated under reduced pressure, and water
  2. additionwas added to the residue
  3. customto collect crystals
  4. filtrationdeposited by filtration
  5. washThe crystals were washed with water
  6. customdried

Sources & evidence

ORD record
ord-2beae094de244f5d962a633e8def4503
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Linked notes

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