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Chemical Structure| 685886-67-3 Chemical Structure| 685886-67-3

Structure of 685886-67-3

Chemical Structure| 685886-67-3

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Product Details of [ 685886-67-3 ]

CAS No. :685886-67-3
Formula : C10H15BO5
M.W : 226.03
SMILES Code : COCC1=CC(OC)=C(B(O)O)C(OC)=C1

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Application In Synthesis of [ 685886-67-3 ]

* 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.

  • Downstream synthetic route of [ 685886-67-3 ]

[ 685886-67-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 685886-67-3 ]
  • [ 13067-94-2 ]
  • [ 1395411-63-8 ]
YieldReaction ConditionsOperation in experiment
1.43 g With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; for 4.0h;Reflux; General procedure: A mixture of crude 13b (5.64 g, 27 mmol), [2,6-dimethoxy-4-(methoxymethyl)phenyl]boronic acid (7.93 g, 35.1 mmol), Pd(PPh3)4 (1.56 g, 1.35 mmol), and Na2CO3 (7.15 g, 67.5 mmol) in a mixture of 1,2-dimethoxyethane (100 mL) and H2O (20 mL) was stirred at reflux temperature for 4 h. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was extracted into ethyl acetate and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (9:1-7:3 n-heptane/ethyl acetate gradient) to afford the title compound 14b as a white solid (1.43 g, 4.04 mmol, 13.2% in two steps). 1H NMR (600 MHz, CDCl3): delta = 3.45 (s, 3H), 3.74 (s, 6H), 4.52 (s, 2H), 6.68 (s, 2H), 7.64 (d, J = 9.1 Hz, 1H), 7.77 (dd, J = 8.3, 7.6 Hz, 1H), 8.35 (d, J = 7.6 Hz, 1H), 8.49 (d, J = 8.3 Hz, 1H), 8.98 (d, J = 9.1 Hz, 1H); 13C NMR (151 MHz, CDCl3): delta = 56.0, 58.2, 74.8, 103.3, 117.3, 120.1, 124.1, 127.0, 127.6, 131.1, 136.7, 141.4, 145.6, 148.4, 157.1, 158.1; IR (KBr): = 2942, 2842, 1611, 1578, 1524, 1457, 1417, 1332, 1229, 1116, 1098, 825 cm-1; HRMS-ESI m/z [M+H]+ calcd for C19H19N2O5+: 355.1289, found: 355.1291.
  • 2
  • [ 61367-62-2 ]
  • [ 685886-67-3 ]
 

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