Triethyl phosphonoacetate → HCID 67249397、化合物

HRID 515730ノート

反応式

HRID 515730 の反応式
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH3:17][O:18][C:19]1[CH:27]=[CH:26][C:25]2[N:24]3[CH2:28][CH2:29][C:30](=O)[C:23]3=[CH:22][C:21]=2[C:20]=1[CH3:32].[NH4+].[Cl-]>CN(C=O)C>[CH3:17][O:18][C:19]1[CH:27]=[CH:26][C:25]2[N:24]3[CH2:28][CH2:29][C:30](=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:23]3=[CH:22][C:21]=2[C:20]=1[CH3:32]

参加物

6

反応物 4

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 672497037-Methoxy-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-one

生成物 1

HCID 67249397HCID 67249397、化合物収率 54.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of ethyl 2-(diethoxyphosphoryl)acetate (1.38 mL, 6.97 mmol) in DMF (2 mL) was added sodium hydride (60% dispersion in mineral oil) (279 mg, 6.97 mmol) at 0° C. The reaction mixture was stirred for 10 min, then 7-methoxy-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-one (500 mg, 2.323 mmol) in DMF (6 mL) was added. The reaction mixture was warmed to room temperature and stirred for 1 h, then heated at 60° C. for 1 h, cooled down, poured into saturated NH4Cl aqueous solution, extracted with ethyl acetate. The combined organics were washed with water, dried over anhydrous Na2SO4, and concentrated. The residue was purified by silica gel column chromatography to give the title compound (361 mg). LCMS m/z=286.2 [M+H]+.

後処理

  1. stirringstirred for 1 h
  2. temperatureheated at 60° C. for 1 h
  3. temperaturecooled down
  4. extractionextracted with ethyl acetate
  5. washThe combined organics were washed with water
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-eaaf330fbb24494b89c9cc983861df88
出典データセット
uspto-grants-2015_08
特許番号
US09108969B2

反応ノート

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