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Cesium carbonate → Methyl 5-methoxynicotinate

HRID 2264156
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HRID 2264156 반응식
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:12](=O)([O-])[O-].[Cs+].[Cs+]>[Cl-].C1([N+](C)(C)C)C=CC=CC=1.C(#N)C>[CH3:12][O:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]
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참가 물질

5

반응물 2

HCID 10796Cesium carbonateHCID 354317Methyl 5-hydroxypyridine-3-carboxylate

생성물 1

HCID 16218325Methyl 5-methoxynicotinate

시약·촉매·용매 2

HCID 67309Phenyltrimethylammonium chloride촉매HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

A mixture of 0.5 g of methyl 5-hydroxynicotinate, 1.2 g (2 equiv) of phenyltrimethylammonium chloride, 4.8 g (3 equiv) of cesium carbonate, and 5 mL of anhydrous acetonitrile was heated to 80° C. for 6 h, cooled, filtered and concentrated under reduced pressure. The residue was taken up in 25 mL of ethyl acetate, filtered and concentrated. Purification by flash chromatography (0-50% ethyl acetate in hexane) gave the product as white crystalline solid: MS (m+1)=168.1; 1H NMR (400 MHz, CDCl3) 8.72 (s, 1H), 8.4 (s, 1H), 7.67 (s, 1H), 3.83 (s, 3H), 3.82 (s, 3H).

후처리

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography (0-50% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-15cb9dd0846b45f9a55572fac05a226f
출처 데이터셋
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07855201B2

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