Methanol → 4-(Hydroxymethyl)pyridin-2(1H)-one

HRID 1475233ノート

反応式

HRID 1475233 の反応式
[O:1]=[C:2]1[CH:7]=[C:6]([C:8](OC)=[O:9])[CH:5]=[CH:4][NH:3]1.[H-].C([Al+]CC(C)C)C(C)C.CO.O>C1COCC1>[OH:9][CH2:8][C:6]1[CH:5]=[CH:4][NH:3][C:2](=[O:1])[CH:7]=1

参加物

6

反応物 4

HCID 887MethanolHCID 962WaterHCID 280755Methyl 2-oxo-1,2-dihydropyridine-4-carboxylateHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 110946104-(Hydroxymethyl)pyridin-2(1H)-one収率 61.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of methyl 2-oxo-1,2-dihydropyridine-4-carboxylate (300 mg, 1.96 mmol) in THF (20 mL) was added diisobutylaluminium hydride (1.0 M in THF, 20 mL, 20 mmol). The mixture was stirred at RT for 3 h, then MeOH (2 mL) and H2O (1 mL) were added. The mixture was stirred at RT for 20 minutes and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (DCM:MeOH=8:1) to afford 4-(hydroxymethyl)pyridin-2(1H)-one as a white solid (150 mg, 61.2%). MS (ES+) C6H7NO2 requires: 125. found: 126 [M+H]+.

後処理

  1. stirringThe mixture was stirred at RT for 20 minutes
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by silica gel chromatography (DCM:MeOH=8:1)

出典と根拠

ORDレコード
ord-b06f4a02a1114cfdb2ed6cb8ab94b19a
出典データセット
uspto-grants-2015_04
特許番号
US09018380B2

反応ノート

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