Ammonium Chloride → 1-oxo-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carbonitrile

HRID 17889

反応式

HRID 17889 の反応式
Br[C:2]1[C:3](=[O:27])[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:8][CH:7]=[C:6]([O:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:5]=2.[Cu][C:29]#[N:30].[Cl-].[NH4+]>CN(C)C=O>[O:27]=[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([O:17][CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:5]=2)[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:2]1[C:29]#[N:30]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 686950762-Bromo-3-phenyl-6-(3-phenylpropoxy)indene-1-oneHCID 178418546HCID 178418546、化合物

生成物 1

HCID 686950891-oxo-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carbonitrile収率 83.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

2-Bromo-3-phenyl-6-(3-phenylpropoxy)indene-1-one (1.0 g, 2.3 mmol) was dissolved in N,N-dimethylformamide (10 ml). Copper (I) cyanide (617 mg, 6.9 mmol) was added thereto and the mixture was stirred for 3 hours at 150° C. The mixture was cooled, and saturated ammonium chloride was added thereto. The organic layer was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography (ethyl acetate:hexane=1:3) to obtain the title compound (700 mg, yield 80%) as a red solid.

後処理

  1. temperatureThe mixture was cooled
  2. extractionThe organic layer was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customthe resulting residue was purified by column chromatography (ethyl acetate:hexane=1:3)

出典と根拠

ORDレコード
ord-be4c3fb850964b1bb1e28c3c67e9cbba
出典データセット
uspto-grants-2010_06
特許番号
US07741323B2

関連ノート

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