Ethyl 2-(propan-2-yl)pyridine-3-carboxylate → (2-Isopropylpyridin-3-yl)methanol

HRID 1688ノート

反応式

HRID 1688 の反応式
[CH:1]([C:4]1[C:9]([C:10](OCC)=[O:11])=[CH:8][CH:7]=[CH:6][N:5]=1)([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH:1]([C:4]1[C:9]([CH2:10][OH:11])=[CH:8][CH:7]=[CH:6][N:5]=1)([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 19690961Ethyl 2-(propan-2-yl)pyridine-3-carboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 19691012(2-Isopropylpyridin-3-yl)methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The 2-isopropyl-3-carboethoxypyridine (400 mg, 2 mmol) in distilled THF (50 mL) under nitrogen was cooled to 0° C. and lithium aluminum hydride (1M in THF) (2.07 mL) was added dropwise. The reaction was stirred for 18 hours at room temperature then cooled to 0° C. and quenched with EtOAc (100 μL), then H2O (100 μL), then 15% NaOH (100 μL), followed by H2O (300 μL). The mixture was filtered and the solvent was removed under reduced pressure. Toluene was added and the solvent was removed under reduced pressure to give the desired 2-isopropyl-3-hydroxymethylpyridine.

後処理

  1. temperaturethen cooled to 0° C.
  2. customquenched with EtOAc (100 μL)
  3. filtrationThe mixture was filtered
  4. customthe solvent was removed under reduced pressure
  5. additionToluene was added
  6. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-13eeac45e3ff4344b45ee3f41e200838
出典データセット
uspto-grants-1998_03
特許番号
US05726172

反応ノート

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