Water → (2-(Benzyloxy)pyridin-4-yl)methanol

HRID 852067노트

반응식

HRID 852067 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:22]=[CH:23][N:24]=1)[C:18](OC)=[O:19])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C(OCC)C>[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH2:18][OH:19])[CH:22]=[CH:23][N:24]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22926252Methyl 2-(benzyloxy)isonicotinate

생성물 1

HCID 16096699(2-(Benzyloxy)pyridin-4-yl)methanol수율 82.7%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

A suspension of lithium aluminum hydride (3.0 g) in diethyl ether (300 mL) was cooled on ice in a nitrogen atmosphere, and then a solution of methyl 2-(benzyloxy)isonicotinate (13.07 g) in diethyl ether (50 mL) wad added dropwise thereinto over 1.5 hours. After stirring for 1 hour, water (3 mL), 5N aqueous sodium hydroxide solution (3 mL) and water (9 mL) were successively added dropwise thereinto under ice-cooling. The insoluble matters were filtered off and washed with diethyl ether, and the filtrate was concentrated. After diethyl ether was added to the residue, the solution was dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale red oil (9.57 g).

후처리

  1. temperaturewas cooled on ice in a nitrogen atmosphere
  2. temperatureunder ice-cooling
  3. filtrationThe insoluble matters were filtered off
  4. washwashed with diethyl ether
  5. concentrationthe filtrate was concentrated
  6. additionAfter diethyl ether was added to the residue
  7. dry with materialthe solution was dried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-732f130ee2ca4185933be294fbcfc74d
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253178B2

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