Potassium Iodide → [Rac]-2-ethoxy-3-[4-(5-methyl-2-thiophen-2-yl-oxazol-4-ylmethoxy)-benzofuran-7-yl]-propionic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH:4]([O:16][CH2:17][CH3:18])[CH2:5][C:6]1[C:14]2[O:13][CH:12]=[CH:11][C:10]=2[C:9]([OH:15])=[CH:8][CH:7]=1.Cl[CH2:21][C:22]1[N:23]=[C:24]([C:28]2[S:29][CH:30]=[CH:31][CH:32]=2)[O:25][C:26]=1[CH3:27].S1C=CC=C1C=O.O=P(Cl)(Cl)Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>>[CH3:1][O:2][C:3](=[O:19])[CH:4]([O:16][CH2:17][CH3:18])[CH2:5][C:6]1[C:14]2[O:13][CH:12]=[CH:11][C:10]=2[C:9]([O:15][CH2:21][C:22]2[N:23]=[C:24]([C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)[O:25][C:26]=2[CH3:27])=[CH:8][CH:7]=1Participants
Reactant 6
Product 1
Procedure
In analogy to the procedure described in example 120 f], 2-ethoxy-3-(4-hydroxy-benzofuran-7-yl)-propionic acid methyl ester (example 120 e]) was reacted with 4-chloromethyl-5-methyl-2-thiophen-2-yl-oxazole (prepared from thiophen-2-carbaldehyde and diacetyl monoxyme followed by treatment with POCl3 in analogy to the procedures described in examples 21 a] and b]) in the presence of potassium carbonate and potassium iodide to yield [rac]-2-ethoxy-3-[4-(5-methyl-2-thiophen-2-yl-oxazol-4-ylmethoxy)-benzofuran-7-yl]-propionic acid methyl ester, which was further saponified in analogy to the procedure described in example 120 f] to yield [rac]-2-ethoxy-3-[4-(5-methyl-2-thiophen-2-yl-oxazol-4-ylmethoxy)-benzofuran-7-yl]-propionic acid as white solid.
Sources & evidence
- ORD record
- ord-dfefb11a730f4938b744bdcc7b9c3d82
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06642389B2
Reaction notes
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