Methyl 2-azidoacetate → Methyl(Z)-2-azido-3-(4-benzyloxy-3-nitrophenyl)acrylate

HRID 896417Notes

Reaction equation

HRID 896417 reaction equation
C[O-].[Na+].[Na].[CH2:5]([O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N:24]([CH2:27][C:28]([O:30][CH3:31])=[O:29])=[N+:25]=[N-:26]>CO.O>[N:24](/[C:27](=[CH:17]\[C:16]1[CH:19]=[CH:20][C:13]([O:12][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[C:14]([N+:21]([O-:23])=[O:22])[CH:15]=1)/[C:28]([O:30][CH3:31])=[O:29])=[N+:25]=[N-:26]

Participants

7

Reactant 4

HCID 4020482Methyl 2-azidoacetateHCID 5360545SodiumHCID 70235544-(Benzyloxy)-3-nitrobenzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 86598196Methyl(Z)-2-azido-3-(4-benzyloxy-3-nitrophenyl)acrylateYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Under argon, to a sodium methoxide solution (prepared from 2.5 g (108.7 mmol) of sodium and 70 ml of methanol) a mixture of 6.1 g (23.7 mmol) of 4-benzyloxy-3-nitrobenzaldehyde and 11.2 g (97.3 mmol) of methyl azidoacetate in 100 ml of methanol is added at 0° C. The mixture is stirred at 0° C. for 5 h, then diluted with 350 ml of water, the precipitated crystalls were filtered off, washed with water and dried to yield 4.93 g (59%) of the title compound. Mp.: 95-96° C. (water).

Workup

  1. additionis added at 0° C
  2. filtrationthe precipitated crystalls were filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-0cfeb709f846437fb94910b63fc4cd7a
Source dataset
uspto-grants-2005_07
Patent number
US06919355B2

Reaction notes

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