Methyl 4-Chloropicolinate → (4-Chloropyridin-2-yl)methanol

HRID 443284

반응식

HRID 443284 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([C:14](OC)=[O:15])[CH:9]=1>C(OCC)C>[Cl:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][OH:15])[CH:9]=1

참가 물질

4

반응물 2

HCID 820890Methyl 4-ChloropicolinateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 2763167(4-Chloropyridin-2-yl)methanol

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a slurry of lithium aluminum hydride (0.45 g, 11.9 mmol) in anhydrous diethyl ether (40 mL) at 0° C., a solution of methyl 4-chloro-pyridine-2-carboxylate (2.0 g, 11.7 mmol) in diethyl ether (30 mL) was added. The resulting mixture was stirred at room temp. overnight, and quenched with successive addition of water (0.45 mL), 15% aqueous NaOH (0.45 mL), and water (1.35 mL). The resultant slurry was stirred at room temp. for 30 min., and filtered through a small plug of Celite. The filtrate was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to provide 4-chloro-2-hydroxymethylpyridine.

후처리

  1. customquenched with successive addition of water (0.45 mL), 15% aqueous NaOH (0.45 mL), and water (1.35 mL)
  2. stirringThe resultant slurry was stirred at room temp. for 30 min.
  3. filtrationfiltered through a small plug of Celite
  4. washThe filtrate was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-a1abab0c1cf143da8767ee054720a160
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05891889

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