2-{[4-(Trimethylsilyl)but-3-yn-1-yl]oxy}pyrimidine → 4-(Trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridine

HRID 2389894노트

반응식

HRID 2389894 반응식
[CH3:1][Si:2]([CH3:15])([CH3:14])[C:3]#[C:4][CH2:5][CH2:6][O:7][C:8]1[N:13]=[CH:12][CH:11]=CN=1>[N+](C1C=CC=CC=1)([O-])=O>[CH3:15][Si:2]([CH3:1])([CH3:14])[C:3]1[CH:11]=[CH:12][N:13]=[C:8]2[O:7][CH2:6][CH2:5][C:4]=12

참가 물질

3

반응물 1

HCID 591793882-{[4-(Trimethylsilyl)but-3-yn-1-yl]oxy}pyrimidine

생성물 1

HCID 591794274-(Trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridine수율 16%

시약·촉매·용매 1

HCID 7416Nitrobenzene용매

실험 절차

A solution of 2-{[4-(trimethylsilyl)but-3-yn-1-yl]oxy}pyrimidine (116 g, 524 mmol) in nitrobenzene (1000 mL) was stirred at 200° C. for 24 hr. The solvent was removed by silica gel column chromatography (ethyl acetate/hexane=13/87→50/50). The residue was diluted with ethyl acetate, and the mixture was extracted twice with 1M hydrochloric acid. The aqueous layer was neutralized with 8M aqueous sodium hydroxide solution and extracted with ethyl acetate. The solvent was evaporated under reduced pressure to give the title compound (16.2 g, yield 14%).

후처리

  1. customThe solvent was removed by silica gel column chromatography (ethyl acetate/hexane=13/87→50/50)
  2. additionThe residue was diluted with ethyl acetate
  3. extractionthe mixture was extracted twice with 1M hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-66e42e340bd64edcb982991f7662555f
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273761B2

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