Water → 2-Chloro-5-methoxy-3-methylpyridine

HRID 1065233

반응식

HRID 1065233 반응식
[H-].[Na+].[Cl:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([OH:11])=[CH:6][N:5]=1.[CH3:12]I.O>CN(C=O)C>[Cl:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([O:11][CH3:12])=[CH:6][N:5]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 128520156-Chloro-5-methylpyridin-3-ol

생성물 1

HCID 128520162-Chloro-5-methoxy-3-methylpyridine수율 101.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Into a flame dried flask under N2 was placed DMF (150 mL), NaH (50% oil dispersion, 4.0 g, 0.08 mol) and 2-chloro-5-hydroxy-3-methylpyridine (11.7 g, 0.08 mol). The solution was stirred at 0°-5° C. until the evolution of H2 ceased and then a solution of CH3I (5.6 mL, 0.09 mol) in DMF (50 mL) was added dropwise. After the addition, the solution was allowed to stir at room temperature overnight. The resulting slurry was added to H2O and extracted with Et2 0 (3×). The organic layer was concentrated and the residue distilled at 85° C. (0.6 mm) to yield 12.8 g of 2-chloro-5-methoxy-3-methylpyridine (95%) as an oil; 1H NMR (CDCl3) δ2.35 (3H, s), 3.8 (3H, s), 7.1 (1H, d, J=3) and 7.9 (1H, d, J=3); MS m/e (M+) 157.

후처리

  1. customInto a flame dried flask under N2
  2. additionAfter the addition
  3. stirringto stir at room temperature overnight
  4. extractionextracted with Et2 0 (3×)
  5. concentrationThe organic layer was concentrated
  6. distillationthe residue distilled at 85° C. (0.6 mm)

출처 및 근거

ORD 기록
ord-dc38a81a69b14da9adb9c1f247a071de
출처 데이터셋
uspto-grants-1982_05
특허 번호
US04329351

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