Methyl 4-Oxo-4,5,6,7-Tetrahydrobenzofuran-5-Carboxylate synthesis
- Product Name:Methyl 4-Oxo-4,5,6,7-Tetrahydrobenzofuran-5-Carboxylate
- CAS Number:164531-75-3
- Molecular formula:C10H10O4
- Molecular Weight:194.18
79-22-1
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164531-75-3
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Yield:164531-75-3 91.9%
Reaction Conditions:
Stage #1: 4-oxo-4,5,6,7-tetrahydrobenzofuranwith lithium hexamethyldisilazane in tetrahydrofuran at -78; for 0.5 h;
Stage #2: methyl chloroformate at 20; for 0.166667 h;
Steps:
2 (2) Methyl 4-oxo-4,5,6,7-tetrahydro-1-benzofuran-5-carboxylate
In dry tetrahydrofuran (10 mL) was dissolved 3.00 g (22.1 mmol) of 6,7-dihydro-1-benzofuran-4(5H)-one obtained in (1), and 48.5 mL (48.5 mmol) of lithium bis(trimethylsilyl)amide (1.0 M tetrahydrofuran solution) was added dropwise to the solution under nitrogen atmosphere at -78C. After stirring at -78C for 30 minutes, 1.87 mL (24.1 mmol) of methyl chlorocarbonate was added dropwise to the mixture, and the reaction mixture was warmed to room temperature and stirred for 10 minutes. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was successively washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed, and the obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane-ethyl acetate, gradient) to obtain 3.93 g (20.3 mmol, Yield: 91.9%) of methyl 4-oxo-4,5,6,7-tetrahydro-1-benzofuran-5-carboxylate.
References:
EP1426365,2004,A1 Location in patent:Page 196
16806-93-2
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164531-75-3
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164531-75-3
15 suppliers
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