Neopentyl alcohol → 2-Fluoro-6-(neopentyloxy)pyridine

HRID 455695

반응식

HRID 455695 반응식
[CH2:1]([OH:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[H-].[Na+].[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12](F)[N:11]=1>CS(C)=O>[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:6][CH2:1][C:2]([CH3:5])([CH3:4])[CH3:3])[N:11]=1

참가 물질

5

반응물 3

HCID 6404Neopentyl alcoholHCID 24758Sodium hydrideHCID 739342,6-Difluoropyridine

생성물 1

HCID 574756582-Fluoro-6-(neopentyloxy)pyridine수율 98.8%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A solution of neopentyl alcohol (1.065 mL, 9.81 mmol) in DMSO (82 mL) was cooled to 0° C. NaH (60% in mineral oil; 0.490 g, 12.26 mmol) were added in one portion, the reaction mixture was warmed to rt and stirred for 20 minutes. 2,6-Difluoropyridine (0.941 mL, 8.175 mmol) was added and the reaction mixture was stirred at overnight. The reaction mixture was quenched with aqueous, saturated ammonium chloride solution, diluted with water and EtOAc. The organic layer was separated, washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure to afford 2-fluoro-6-(neopentyloxy)pyridine (1.48 g, 8.08 mmol) as a colorless liquid.

후처리

  1. stirringthe reaction mixture was stirred at overnight
  2. customThe reaction mixture was quenched with aqueous, saturated ammonium chloride solution
  3. additiondiluted with water and EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-6ebbf77db7b74968bc53b4b25510495f
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497264B2

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