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4-(3-FLUORO-PHENYL)-3-OXO-BUTYRIC ACID METHYL ESTER synthesis
- Product Name:4-(3-FLUORO-PHENYL)-3-OXO-BUTYRIC ACID METHYL ESTER
- CAS Number:944993-11-7
- Molecular formula:C11H11FO3
- Molecular Weight:210.2
Yield:944993-11-7 51%
Reaction Conditions:
Stage #1: (3-fluorophenyl)acetic acidwith 1,1'-carbonyldiimidazole in tetrahydrofuran at 20; for 1 h;
Stage #2: ethyl potassium malonatewith magnesium chloride in tetrahydrofuran at 20;
Steps:
8.A
3-Fluorophenylacetic acid (10.2 g, 66.0 mmol) was dissolved in THF (200 mL) and to it CDI (12.8 g, 79.2 mmol) was added. The resulting solution was stirred at room temperature for 1 h. MgCl2 (6.2 g, 65.4 mmol) and monomethyl monopotassium malonate (15.4 g, 98.3 mmol) was added. The resulting mixture was stirred at room temperature overnight. Water was added and extracted with DCM, dried (MgSO4), filtered and concentrated. The residue was purified by silica gel chromatography (eluted with 5% EtOAc in hexanes) to give Compound 101a (7.0 g, 51%) as a yellow oil.
References:
US2007/173495,2007,A1 Location in patent:Page/Page column 48