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

HRID 19538

反応式

HRID 19538 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.[CH3:28][N:29](C)C=O>[Cu+]>[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:28]#[N:29]

参加物

4

反応物 2

HCID 6228DimethylformamideHCID 686950762-Bromo-3-phenyl-6-(3-phenylpropoxy)indene-1-one

生成物 1

HCID 686950891-oxo-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carbonitrile収率 80%

試薬・触媒・溶媒 1

HCID 104815Copper(1+)触媒

反応条件

温度
150 °C

実験手順

2-Bromo-3-phenyl-6-(3-phenyl-propoxy)-indene-1-one (1.0 g, 2.3 mmol) obtained in Step 2 was dissolved in N,N-dimethyl formamide (10 mL), copper(I) cyamide (617 mg, 6.9 mmol) was added thereto, and the mixture was stirred for 3 hrs at 150° C., followed by cooling. The resulting mixture was washed with saturated ammonium chloride and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography (ethyl acetate:hexane=1:3) to obtain 700 mg of the titled compound (yield: 80%) as a red solid.

後処理

  1. temperatureby cooling
  2. washThe resulting mixture was washed with saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under a reduced pressure
  7. customThe resulting residue was purified by flash chromatography (ethyl acetate:hexane=1:3)

出典と根拠

ORDレコード
ord-25ef1506204e440cafabec79ffa9cfc6
出典データセット
uspto-grants-2010_06
特許番号
US07745439B2

関連ノート

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