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

HRID 19538

반응식

HRID 19538 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 104815Copper(1+)촉매

반응 조건

온도
150 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-25ef1506204e440cafabec79ffa9cfc6
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745439B2

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