Vanillin → Ethyl 5-{4-[(4-formyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}thiophene-2-carboxylate
Reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[S:13][C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].[O:19]=[CH:20][C:21]1[CH:29]=[CH:28][C:26]([OH:27])=[C:23]([O:24][CH3:25])[CH:22]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH:20]([C:21]1[CH:29]=[CH:28][C:26]([O:27][CH2:2][C:3]2[N:4]=[C:5]([C:9]3[S:13][C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][CH:10]=3)[O:6][C:7]=2[CH3:8])=[C:23]([O:24][CH3:25])[CH:22]=1)=[O:19]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of ethyl 5-(4-chloromethyl-5-methyl-1,3-oxazol-2-yl)thiophene-2-carboxylate (5.0 g), vanillin (2.66 g), anhydrous potassium carbonate (2.42 g) and N,N-dimethylformamide (50 mL) was stirred at 90° C. for 2 hrs. Water was poured into the reaction mixture, and the precipitated crystals were collected by filtration, and washed with diethyl ether. The obtained crystals were recrystallized from acetone-hexane to give ethyl 5-{4-[(4-formyl-2-methoxyphenoxy)methyl]-5-methyl-1,3-oxazol-2-yl}thiophene-2-carboxylate as colorless prism crystals (5.75 g, yield 82%). melting point: 155-156° C.
Workup
- filtrationthe precipitated crystals were collected by filtration
- washwashed with diethyl ether
- customThe obtained crystals were recrystallized from acetone-hexane
Sources & evidence
- ORD record
- ord-d1940f8112f04e2d9ef5415533caface
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07368578B2
Reaction notes
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