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CAS No. : | 54442-11-4 | MDL No. : | MFCD12179181 |
Formula : | C10H10O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 178.18 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.2% | With hydrogenchloride; In water; at 20℃; | a) (R,S)-2,3-Dihydro-benzofuran-2-carboxylic acid methyl ester (68a) To a solution of (R,S)-2,3-Dihydro-benzofuran-2-carboxylic acid 54a (18 g) in methanol was added hydrogen chloride (200 mL, 2.0 M in ether). The reaction mixture was stirred at room temperature overnight and concentrated to give the title compound (19 g, 97.2%). 1H NMR (400 MHz, CDCl3) delta: 7.16 (m, 2H), 6.89 (m, 2H), 5.20 (dd, 1H), 3.80 (s, 3H), 3.55 (dd, 1H), 3.37 (dd, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.1% | In diethyl ether; at 20℃; for 0.5h; | To a solution of <strong>[1914-60-9]2,3-dihydro-1-benzofuran-2-carboxylic acid</strong> (1.033 g, 6.29 mmol) (Oakwood, CAS 1914-60-9) in diethyl ether (31.5 mL) was added (trimethylsilyl)diazomethane (3.15 mL, 6.29 mmol) dropwise. The reaction was stirred at room temperature for 30 minutes. The solvent was removed and the crude material was purified using a 40 g silica gel cartridge, eluting with a gradient of 5-100% ethyl acetate/heptanes to provide the title compound (0.562 g, 3.15 mmol, 50.1% yield). 1H NMR (501 MHz, DMSO-d6) delta 7.21 (dq, J=7.3, 1.3 Hz, 1H), 7.12 (td, J=7.6, 1.2 Hz, 1H), 6.89-6.80 (m, 2H), 5.33 (dd, J=10.8, 6.1 Hz, 1H), 3.69 (s, 3H), 3.62-3.50 (m, 1H), 3.27 (dd, J=16.1, 6.1 Hz, 1H). |