Reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[N+:20]=[N-:21].C[O-].[Na+].[Na]>CO>[CH3:26][O:25][C:23](=[O:24])[C:22]([N:19]=[N+:20]=[N-:21])=[CH:13][C:12]1[CH:15]=[CH:16][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([O:17][CH3:18])[CH:11]=1Participants
6
Conditions
- Temperature
- 0 °C
Procedure
A solution of the 4-Benzyloxy-3-methoxy-benzaldehyde (12.0 g, 49.6 mmol) and methyl azidoacetate (23 g, 0.200 mol) in methanol (50 mL) was added over 30 min to a cooled (ice-salt bath) solution of sodium methoxide which had been prepared from addition of methanol (80 mL) to sodium (3.4 g, 0.149 mol). The reaction mixture was stirred at 0° C. for 45 min, during this time a thick cream precipitate formed, and then stood in the freezer overnight. Ice-cold water was added and the precipitate was removed by filtration and dried to give methyl-2-azido-3-[4′-(benzyloxy)-3′-methoxyphenyl]prop-2-enoate (55) (12.2 g, 73%) which was used in the next step without purification.
Workup
- customformed
- customstood in the freezer overnight
- additionIce-cold water was added
- customthe precipitate was removed by filtration
- customdried
Sources & evidence
- ORD record
- ord-d9e8ac3d46b14af1810494a565aed42a
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07094798B1
Linked notes
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