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Water → ethyl 3-[(1E)-4-methoxybut-1-en-1-yl]imidazo[1,2-a]pyridine-2-carboxylate

HRID 1509531
ノート
印刷プレビュー

反応式

HRID 1509531 の反応式
[Br-].[CH3:2][O:3][CH2:4][CH2:5][CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH:32]([C:34]1[N:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]2=[N:36][C:35]=1[C:43]([O:45][CH2:46][CH3:47])=[O:44])=O.O>C1COCC1>[CH3:2][O:3][CH2:4][CH2:5]/[CH:6]=[CH:32]/[C:34]1[N:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]2=[N:36][C:35]=1[C:43]([O:45][CH2:46][CH3:47])=[O:44]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 10704014Ethyl 3-formylimidazo[1,2-a]pyridine-2-carboxylateHCID 21458797(3-Methoxypropyl)triphenylphosphonium bromideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 58355141ethyl 3-[(1E)-4-methoxybut-1-en-1-yl]imidazo[1,2-a]pyridine-2-carboxylate収率 12%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a suspension of (3-methoxypropyl) (triphenyl)phosphonium bromide (3.56 g) in THF (50 ml) was added potassium tert-butoxide (0.38 g) at −78° C., and the mixture was stirred at the same temperature for 30 min. Ethyl 3-formylimidazo[1,2-a]pyridine-2-carboxylate (1.7 g) was added to the reaction mixture, and the mixture was stirred at room temperature for 12 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate was concentrated under reduced pressure to give the object product (256 mg).

後処理

  1. stirringthe mixture was stirred at room temperature for 12 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washa fraction eluted with ethyl acetate
  7. concentrationwas concentrated under reduced pressure

出典と根拠

ORDレコード
ord-e574cc6a85834b4fba85b187fa81780f
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09221836B2

反応ノート

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