Potassium Carbonate → 2Z-ethoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-4-yl}-acrylic acid ethyl ester
Reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[C:21]2[S:22][CH:23]=[CH:24][C:20]=2[C:19](C=O)=[CH:18][CH:17]=1.[Cl-].[CH2:28]([O:30][CH:31]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH3:29].[C:56](=O)([O-])[O-].[K+].[K+]>CC(O)C>[CH2:35]([O:34][C:32](=[O:33])/[C:31](/[O:30][CH2:28][CH3:29])=[CH:56]/[C:19]1[C:20]2[CH:24]=[CH:23][S:22][C:21]=2[C:16]([O:15][CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])=[CH:17][CH:18]=1)[CH3:36]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In analogy to the procedure described in example 91 c], 7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophene-4-carbaldehyde (example 98 a]) was treated with (ethoxy-ethoxycarbonyl-methyl)-triphenyl-phosphonium chloride [Tetrahedron 50(25), 7543-56(1994)]in 2-propanol in the presence of potassium carbonate to yield the 2Z-ethoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-4-yl}-acrylic acid ethyl ester. The 2Z-ethoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-4-yl}-acrylic acid ethyl ester was further saponified in analogy to the procedure described in example 99 to yield the 2Z-ethoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-4-yl}-acrylic acid as colorless solid.
Sources & evidence
- ORD record
- ord-0175798bacc0419287733ceee53aef4d
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06642389B2
Reaction notes
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