Sodium hydride → 5-(t-Butoxycarbonylmethyl)oxy-2-hydroxymethylpyridine

HRID 1940382노트

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HRID 1940382 반응식
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1.[H-].[Na+].Br[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>CN(C=O)C.C(OCC)(=O)C>[C:17]([O:16][C:14]([CH2:13][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 4194905-Hydroxy-2-hydroxymethylpyridine

생성물 1

HCID 214660515-(t-Butoxycarbonylmethyl)oxy-2-hydroxymethylpyridine수율 85%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

The solution of 5-hydroxy-2-hydroxymethylpyridine (5.0 g) in DMF (10 ml) was titrated under ice-cooling in the suspension of sodium hydride (60% purity, 1.6 g) in DMF (10 ml). After 10 minutes, the mixture was heated to room temperature and stirred for 15 minutes. After t-butyl bromoacetate (6 ml) was added to the mixture under ice-cooling, the resulting mixture was stirred under ice-cooling for 10 minutes and at room temperature for 45 minutes. The reaction mixture was diluted with ethyl acetate, washed with water and brine and dried over anhydrous magnesium sulfate. After the solvents were removed by distillation, the residue was purified by column chromatography on silica gel with an eluent system of chloroform→chloroform:methanol=50:1 to give 8.16 g of 5-(t-butoxycarbonylmethyl)oxy-2-hydroxymethylpyridine (yield, 85%).

후처리

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred under ice-
  3. temperaturecooling for 10 minutes and at room temperature for 45 minutes
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter the solvents were removed by distillation
  7. customthe residue was purified by column chromatography on silica gel with an eluent system of chloroform→chloroform

출처 및 근거

ORD 기록
ord-0e7f45ad76aa42c3b5ebd1d5d8f5dd2e
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05698692

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