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1-Propanol → propyl 3-[3-(2-oxo-2-propoxyethyl)-1H-indol-2-yl]propanoate

HRID 476223
ノート
印刷プレビュー

反応式

HRID 476223 の反応式
CS(O)(=O)=O.O=[C:7]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)N=[C:10](CCC(OCC)=O)[CH2:9][CH2:8]1.[OH-:26].[Na+].[CH2:28]([OH:31])[CH2:29][CH3:30]>>[O:31]=[C:28]([O:31][CH2:28][CH2:29][CH3:30])[CH2:29][C:30]1[C:14]2[C:13](=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:12][C:7]=1[CH2:8][CH2:9][C:10]([O:31][CH2:28][CH2:29][CH3:30])=[O:26]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 4

HCID 10311-PropanolHCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 21630617Ethyl 3-(6-oxo-1-phenyl-1,4,5,6-tetrahydropyridazin-3-yl)propanoate

生成物 1

HCID 59487250propyl 3-[3-(2-oxo-2-propoxyethyl)-1H-indol-2-yl]propanoate収率 79%

反応条件

温度
80 °C

実験手順

Methanesulfonic acid (1.15 equiv.) was added to a stirred solution of ethyl 3-(6-oxo-1-phenyl-1,4,5,6-tetrahydropyridazin-3-yl)propanoate from Step 1 in n-propanol (1.1 M). The mixture was stirred overnight at 80° C. The mixture was cooled to room temperature and neutralized with aqueous 1N NaOH (1 equiv.). Final mixture was concentrated under vacuum, diluted with toluene and concentrated again. The residue was purified by column chromatography on silica gel using automatized gradiant pump system CombiFlashRF (Teledyne ISCO) eluting with ethyl acetate/hexane (0:100 to 60:40) to give the title compound (79%) as a brown oil.

後処理

  1. concentrationFinal mixture was concentrated under vacuum
  2. additiondiluted with toluene
  3. concentrationconcentrated again
  4. customThe residue was purified by column chromatography on silica gel using automatized gradiant pump system CombiFlashRF (Teledyne ISCO)
  5. washeluting with ethyl acetate/hexane (0:100 to 60:40)

出典と根拠

ORDレコード
ord-0b4718e0eecc4e0bb88ad95c30455e85
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08637671B2

反応ノート

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