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3-Hydroxy-2,6-dimethoxypyridine synthesis
- Product Name:3-Hydroxy-2,6-dimethoxypyridine
- CAS Number:885963-28-0
- Molecular formula:C7H9NO3
- Molecular Weight:155.15
![2,6-Dimethoxypyridine-3-boronic acid](/CAS/GIF/221006-70-8.gif)
221006-70-8
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![3-Hydroxy-2,6-dimethoxypyridine](/CAS/20180703/GIF/885963-28-0.gif)
885963-28-0
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Yield:885963-28-0 90%
Reaction Conditions:
Stage #1: 2,6-dimethoxypyridine-3-boronic acidwith peracetic acid;acetic acid in tetrahydrofuran at 0 - 20; for 2 h;
Stage #2: with sodium sulfite in tetrahydrofuran at 20; for 0.5 h;
Steps:
2,6-Dimethoxypyridin-3-ol (57)
To a solution of 56 (8.00 g, 43.49 mmol) in THF (150 mL, dist. Na) at 0 °C was added dropwise 32% peracetic acid in acetic acid (21.53 mL, 86.98 mmol) over 10 min. The resultant solution was stirred at r.t. for 2 h. A 10% solution of sodium sulfite (75 mL) was then added and the mixture stirred at r.t. for 0.5 hour. The solvent was evaporated and the residue partitioned between EtOAc and water. The aqueous layer was extracted twice and the organic layer dried and evaporated. Column chromatography with 9: 1 hexanes/EtOAc afforded the product 57. Yield = 6.05 g, 90%. 1H NMR (CDC13) δ 7.12 (1H, d, J = 8.3 Hz), 6.21 (1H, d, J = 8.2 Hz), 4.90 (1H, s), 7.00 (3H, s), 3.86 (3H, s). Found: [M+H]=156.7
References:
WO2017/155909,2017,A1 Location in patent:Paragraph 0112
![2,6-Dimethoxypyridine](/CAS/GIF/6231-18-1.gif)
6231-18-1
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![3-Bromo-2,6-dimethoxypyridine](/CAS/GIF/13445-16-4.gif)
13445-16-4
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$9.00/1g
![3-Hydroxy-2,6-dimethoxypyridine](/CAS/20180703/GIF/885963-28-0.gif)
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