1,3-Benzodioxole-4-carboxaldehyde → HCID 53799897, compound

HRID 1249946Notes

Reaction equation

HRID 1249946 reaction equation
[CH2:1]1[O:11][C:10]2[C:3](=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=O)[O:2]1.[CH3:12][O:13][C:14](=[O:19])[CH2:15][N:16]=[N+:17]=[N-:18].C[O-].[Na+]>CO>[N:16]([C:15](=[CH:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:10]2[O:11][CH2:1][O:2][C:3]=12)[C:14]([O:13][CH3:12])=[O:19])=[N+:17]=[N-:18]

Participants

5

Reactant 3

HCID 822641,3-Benzodioxole-4-carboxaldehydeHCID 4020482Methyl 2-azidoacetateHCID 10942334Sodium Methoxide

Product 1

HCID 53799897HCID 53799897, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,3-methylenedioxy benzaldehyde (15.76 g, 104 mmol) and methylazidoacetate (48.38 g, 419 mmol) in methanol was cooled to −15° C. using an ice/acetone bath. The resulting solution was then treated over one hour with sodium methoxide (96 ml) at a rate that maintained the temperature below −10° C. After 3 hours, the solution was stored at 5° C. for two days to give crystalline material which was filtered off and washed with hexane.

Workup

  1. temperaturemaintained the temperature below −10° C
  2. waitthe solution was stored at 5° C. for two days
  3. customto give crystalline material which
  4. filtrationwas filtered off
  5. washwashed with hexane

Sources & evidence

ORD record
ord-0e062c135db140dabd0c6c79bdd8204f
Source dataset
uspto-grants-2002_01
Patent number
US06335360B1

Reaction notes

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