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

HRID 2389894ノート

反応式

HRID 2389894 の反応式
[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

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7416Nitrobenzene溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-66e42e340bd64edcb982991f7662555f
出典データセット
uspto-grants-2012_09
特許番号
US08273761B2

反応ノート

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