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Dimethylformamide → Methyl 3-methoxypyridine-2-carboxylate

HRID 341484
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HRID 341484 반응식
[OH:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:12](=O)([O-])[O-].[K+].[K+].IC.CN(C=O)C>O>[CH3:12][O:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 819341Methyl 3-Hydroxy-2-pyridinecarboxylate2회

생성물 1

HCID 20474189Methyl 3-methoxypyridine-2-carboxylate수율 45%

시약·촉매·용매 1

HCID 962Water용매
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실험 절차

A mixture of methyl 3-hydroxypyridine-2-carboxylate (Intermediate 96, 1.2 g, 7.8 mmol), potassium carbonate (1.2 g, 8.7 mmol), iodomethane (0.63 ml, 1.0 mmol) and DMF (10 ml) was stirred overnight. The mixture was diluted with water (20 ml) and extracted with ethyl acetate (2×20 ml). The combined organic extracts were washed with water and concentrated under vacuum. The residue (0.82 g) was purified by flash column chromatography (5 g silica; heptane-ethyl acetate, 1:0-5:1-2:1) to give the title compound as a clear oil (0.58 g, 45%). Method C HPLC-MS: MH+ requires m/z=168. Found: m/z=168, Rt=0.76 min (100%).

후처리

  1. extractionextracted with ethyl acetate (2×20 ml)
  2. washThe combined organic extracts were washed with water
  3. concentrationconcentrated under vacuum
  4. customThe residue (0.82 g) was purified by flash column chromatography (5 g silica; heptane-ethyl acetate, 1:0-5:1-2:1)

출처 및 근거

ORD 기록
ord-e80ac57eeb7646c29b92b8f930960504
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08895733B2

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