4-(3-Pyridyl)-1-butanol synthesis
- Product Name:4-(3-Pyridyl)-1-butanol
- CAS Number:60753-14-2
- Molecular formula:C9H13NO
- Molecular Weight:151.21
138487-20-4
60753-14-2
General procedure for the synthesis of 4-(3-pyridinyl)-1-butyn-1-ol from 4-(3-pyridinyl)-3-butyn-1-ol: 4-(3-pyridinyl)-3-butyn-1-ol (0.32 g, 2.2 mmol) was dissolved in EtOH (44 mL) and passed through a H-Cube?flow hydrogenation reactor fitted with 10% Pd/C catalyst to carry out the hydrogenation reaction (flow rate : 1.0 mL/min; pressure: 1.0 bar; temperature: 3.5°C). After completion of the reaction, the output solution was concentrated to dryness to give an oily residue (0.31 g). Purification by conventional silica gel fast chromatography (eluent: CH2Cl2/MeOH, 95:5) afforded pure 4-(3-pyridyl)-1-butanol (0.294 g, 89% yield) as a colorless liquid. rf = 1.16 mm. m/z MS (ESI) m/z: 152 [M-H]-. 1H NMR (DMSO-d6) δ: 8.43 (m. 1H), 8.38 (dd, 1H, J = 4.8, 1.5 Hz), 7.61 (dt, 1H, J = 7.8, 2.1 Hz), 7.30 (dd, 1H, J = 7.8, 4.8 Hz), 4.37 (t, 1H, J = 5.2 Hz), 3.41 (q, 2H, J = 5.2 Hz), 2.59 (t, 2H, J = 7.7 Hz), 1.64-1.55 (m, 2H), 1.47-1.38 (m, 2H).
138487-20-4
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Yield:60753-14-2 99%
Reaction Conditions:
with palladium 10% on activated carbon;hydrogen in methanol at 20;
References:
Hoang, Van-Hai;Tran, Phuong-Thao;Cui, Minghua;Ngo, Van T. H.;Ann, Jihyae;Park, Jongmi;Lee, Jiyoun;Choi, Kwanghyun;Cho, Hanyang;Kim, Hee;Ha, Hee-Jin;Hong, Hyun-Seok;Choi, Sun;Kim, Young-Ho;Lee, Jeewoo [Journal of Medicinal Chemistry,2017,vol. 60,# 6,p. 2573 - 2590] Location in patent:supporting information
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60753-13-1
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