Water → 2-Bromo-3-(isopropoxymethyl)-pyridine

HRID 1517580노트

반응식

HRID 1517580 반응식
[CH:1]([OH:4])([CH3:3])[CH3:2].[H-].[Na+].[Br:7][C:8]1[C:13]([CH2:14]Br)=[CH:12][CH:11]=[CH:10][N:9]=1.O>CN(C)C=O>[Br:7][C:8]1[C:13]([CH2:14][O:4][CH:1]([CH3:3])[CH3:2])=[CH:12][CH:11]=[CH:10][N:9]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 3776IsopropanolHCID 24758Sodium hydrideHCID 109010782-Bromo-3-(bromomethyl)pyridine

생성물 1

HCID 582685582-Bromo-3-(isopropoxymethyl)-pyridine수율 66.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of isopropyl alcohol (7.31 mL, 95.65 mmol) in dimethylformamide (50 mL) at 0° C. is added sodium hydride (3.63 g, 90.87 mmol) and the mixture is stirred at room temperature for 30 minutes (this reaction is run using a shield as special protection). Then, 2-bromo-3-bromomethyl-pyridine (6 g, 23.91 mmol) in 10 mL of dimethylformamide is added via syringe and the mixture is stirred at room temperature for 1 h. Water is added and the mixture is extracted with ethyl acetate, washed with brine and water, dried over magnesium sulfate, filtered and the solvent evaporated under reduced pressure. The crude material is purified by normal phase Isco chromatography using ethyl acetate and hexane as eluent (gradient of 5 to 25% of ethyl acetate) to yield 3.67 g of the title compound. MS (m/z): 230, 232 (M+1, M+3)

후처리

  1. stirringthe mixture is stirred at room temperature for 1 h
  2. extractionthe mixture is extracted with ethyl acetate
  3. washwashed with brine and water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customThe crude material is purified by normal phase Isco chromatography

출처 및 근거

ORD 기록
ord-ee819b65e6d34b019dbb10a3f8101b9e
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232289B2

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