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CAS No. : | 301699-39-8 | MDL No. : | MFCD01114648 |
Formula : | C9H13BO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WZUCSPWZHRVOSD-UHFFFAOYSA-N |
M.W : | 180.01 | Pubchem ID : | 3817586 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
With copper(II) nitrate hexahydrate; N,N,N,N,-tetramethylethylenediamine; oxygen; In methanol; at 20℃; for 24h; | General procedure: To a solution of 3 (100 mg, 0.30 mmol) and (4-methoxy-3,5-dimethylphenyl)boronic acid(108 mg, 0.60 mmol) in dry MeOH (5.0 mL) was added Cu(NO3)2 (H2O)6 (800 muL of 0.14 Msolution in dry MeOH, 0.11 mmol) and TMEDA (800 muL of a 0.14 M solution in dry MeOH,0.11 mmol). The resulting mixture was stirred for 24 h at ambient temperature under O2.Volatiles were evaporated and the crude material was re-dissolved in CH2Cl2 and washed withsaturated EDTA (aq). The organic layer was dried over Na2SO4 and volatiles were removedunder reduced pressure. The crude material was dissolved in MeOH (4.0 mL). To this solution K2CO3 (100 mg, 0.72 mmol) was added and the mixture was stirred for 12 h at ambienttemperature. Volatiles were evaporated and the crude was partitioned (CH2Cl2//H2O). Theorganic layer was separated and dried over Na2SO4. Flash chromatography (70%EtOAc/Hexanes) gave 6c (27 mg, 0.73 mmol, 24%). 1H NMR (CDCl3, 500MHz) delta 8.82 (s, 1H),8.24 (s, 1H), 8.15 (s, 1H), 7.30 (s, 2H), 3.77 (s, 3H), 2.38 (s, 6H), 1.58 (s, 9H); 13C NMR(CDCl3, 125 MHz) delta 157.2, 153.6, 150.2, 149.8, 141.7, 132.9, 129.5, 124.2, 82.3, 59.8, 28.2,16.3; HRMS [M+H] = 370.1875; C19H24N5O3 = 370.1879. |