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

HRID 1688노트

반응식

HRID 1688 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-13eeac45e3ff4344b45ee3f41e200838
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726172

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