Sodium Hydroxide → (6-Phenylpyridin-3-yl)methanol

HRID 914456노트

반응식

HRID 914456 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:13][CH:12]=1)C.[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.O>[C:17]1([C:14]2[N:13]=[CH:12][C:11]([CH2:10][OH:9])=[CH:16][CH:15]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 11096332Ethyl 6-phenylnicotinateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 22254216(6-Phenylpyridin-3-yl)methanol수율 99.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Lithium aluminum hydride (3.50 g) was suspended in tetrahydrofuran (200 mL), 6-phenylnicotinic acid ethyl ester (21.0 g) synthesized in Reference Example 19 was added under ice-cooling, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was ice-cooled, water (5 mL) and aqueous sodium hydroxide solution (1 mol/L, 10 mL) were successively added dropwise. After warming to room temperature, the mixture was stirred for 1 hr. Anhydrous sodium sulfate was added to the reaction mixture, the mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1 to 1:3) to give the title compound (17.0 g) as a colorless oil.

후처리

  1. additionwas added under ice-
  2. temperaturecooling
  3. temperaturecooled
  4. temperatureAfter warming to room temperature
  5. stirringthe mixture was stirred for 1 hr
  6. filtrationthe mixture was filtered through celite
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1 to 1:3)

출처 및 근거

ORD 기록
ord-b291f32fafb14751874c9cbdacd2d01c
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026370B2

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