Iodoethane → 2-Ethoxy-4-fluorobenzaldehyde
Reaction equation
COC(=O)C(OCC)CC1C2SC=CC=2C(O)=CC=1.[CH2:20]([O:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[C:30]1[O:31]C(C)=C(CCO)N=1)[CH3:21].C(I)C.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:20]([O:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[CH:30]=[O:31])[CH3:21]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
In analogy to the procedure described in example 17 a], [rac]-2-ethoxy-3-(4-hydroxy-benzo[b]thiophen-7-yl)-propionic acid methyl ester was reacted with 2-[2-(2-ethoxy-4-fluoro-phenyl)-5-methyl-oxazol-4-yl]-ethanol (prepared from 4-fluoro-2-hydroxy-benzaldehyde [J. Chem. Soc., Perkin Trans. 1 (1994), (13), 1823-31] by i) treatment with ethyl iodide, potassium carbonate in N,N-dimethylformamide to give 2-ethoxy-4-fluoro-benzaldehyde; ii) conversion of the 2-ethoxy-4-fluoro-benzaldehyde into 2-[2-(2-ethoxy-4-fluoro-phenyl)-5-methyl-oxazol-4-yl]-ethanol in analogy to the sequence described in examples 21 a] to 21 e]) in the presence of triphenylphosphine and DEAD (diethyl azodicarboxylate) to yield [rac]-2-ethoxy-3-(4-{2-[2-(2-ethoxy-4-fluoro-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-benzo[b]thiophen-7-yl)-propionic acid methyl ester, which was further saponified in analogy to the procedure described in example 91 e] to yield [rac]-2-ethoxy-3-(4-{2-[2-(2-ethoxy-4-fluoro-phenyl)-5-methyl-oxazol-4-yl]-ethoxy-}-benzo[b]thiophen-7-yl)-propionic acid as light yellow solid.
Sources & evidence
- ORD record
- ord-0d83d4ffcccd442ea7405adc85cd96d5
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06642389B2
Reaction notes
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