Benzyl Alcohol → 6-((Benzyloxy)carbonyl)picolinic acid

HRID 1397288ノート

反応式

HRID 1397288 の反応式
[N:1]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=[CH:3][C:2]=1[C:10]([OH:12])=[O:11].[CH2:13](O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.OS(O)(=O)=O>O>[CH2:13]([O:11][C:10]([C:2]1[N:1]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=[CH:4][CH:3]=1)=[O:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

5

反応物 3

HCID 244Benzyl AlcoholHCID 1118Sulfuric AcidHCID 103672,6-Pyridinedicarboxylic acid

生成物 1

HCID 153299296-((Benzyloxy)carbonyl)picolinic acid収率 30%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 2,6-pyridinedicarboxylic acid (10 g, 0.06 mol) and benzyl alcohol (68 mL, 0.66 mol) were taken in water (25 mL), and concentrated H2SO4 (3.5 mL) was added. The reaction mixture was refluxed for 10 h and further allowed to stir at room temperature for 24 h. The reaction mixture was concentrated under reduced pressure and the organic product was extracted with CHCl3. The solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 5% MeOH in CH2Cl2) to afford 6-((benzyloxy)carbonyl)picolinic acid (4.6 g, yield 30%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 13.54 (br s, 1H), 8.29-8.24 (m, 2H), 8.20-8.16 (m, 1H), 7.52-7.50 (m, 2H), 7.44-7.36 (m, 3H), 5.43 (s, 2H). MS (ESI) m/z: Calculated for C14H11NO4: 257.07. found: 258.2 (M+H)+.

後処理

  1. temperatureThe reaction mixture was refluxed for 10 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionthe organic product was extracted with CHCl3
  4. customThe solvent was removed under reduced pressure
  5. customthe crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 5% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-781e6510ec674b579a8ba234add069fd
出典データセット
uspto-grants-2014_12
特許番号
US08901156B2

反応ノート

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