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Yield | Reaction Conditions | Operation in experiment |
48% |
Stage #1: for 18.00 h; Reflux Stage #2: at 20℃; for 4.00 h; |
[00140] 1-Ethynyl-4-methylbenzene (0.50 mL, 3.94 mmol, 1.00 eq) and catecholborane (0.50 mL, 4.73 mmol, 1 .20 eq) were dissolved in THF (1 .5 mL) and the mixture was refluxed for 18h. The solvent was evaporated and then H20 (1 mL) was added. The suspension was vigorously stirred for 4 h at room temperature. The solid was filtered and recrystallized with water. (E)-5-phenylpent-1-en-1-ylboronic acid (309.4 mg, 1.90 mmol, 48percent) was then filtered and dried under vacuum.1H NMR (400 MHz, DMSO-d6) OH /ppm 7.73 (5, 2H), 7.36 (d, J= 7.9 Hz, 2H), 7.18 (d, J= 7.9 Hz, 2H), 6.05 (d, J= 18.3 Hz, 1H), 2.31 (5, 3H).13C NMR (101 MHz, DMSO) Oc /ppm: 146.2, 138.4, 135.4, 129.8 (20), 127.0 (20), 21 .3. |
Reference:
[1] Patent: WO2016/198836, 2016, A1. Location in patent: Paragraph 00140
[2] Organic Letters, 2014, vol. 16, # 13, p. 3444 - 3447
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Reference:
[1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 11, p. 2803 - 2807
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 13, p. 2133 - 2138
[3] Angewandte Chemie - International Edition, 2011, vol. 50, # 2, p. 519 - 522
[4] Australian Journal of Chemistry, 2011, vol. 64, # 1, p. 62 - 67
[5] Organic and Biomolecular Chemistry, 2015, vol. 13, # 26, p. 7136 - 7139
[6] Advanced Synthesis and Catalysis, 2018, vol. 360, # 19, p. 3667 - 3671