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Potassium Carbonate → 5-Methoxy-3-phenyl-1H-inden-1-one

HRID 331388
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HRID 331388 반응식
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:19])/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O.Cl[Pd]Cl>[CH3:9][O:8][C:6]1[CH:7]=[C:2]2[C:3](=[CH:4][CH:5]=1)[C:10](=[O:19])[CH:11]=[C:12]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 70310518HCID 70310518, 화합물

생성물 1

HCID 703155925-Methoxy-3-phenyl-1H-inden-1-one수율 63%

시약·촉매·용매 3

HCID 24290Palladium Chloride촉매HCID 6228Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

To a solution of (E)-1-(2-bromo-4-methoxyphenyl)-3-phenyl-2-propen-1-one (6.0 g, 18.91 mmol) obtained in Step 2 in DMF (15 mL) was added PPh3 (1.46 g, 5.68 mmol, 0.3 eq), K2CO3 (5.23 g, 37.83 mmol, 2 eq), and PdCl2 (335 mg, 1.89 mmol, 0.1 eq). The reaction vial was heated to 110° C. for 3 h. After cooling to room temperature, the reaction mixture was diluted with EtOAc and filtered through a Celite pad. The solution was washed with H2O and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexanes=1:5) to afford the desired product (2.8 g, 63%).

후처리

  1. customThe reaction
  2. temperatureAfter cooling to room temperature
  3. filtrationfiltered through a Celite pad
  4. washThe solution was washed with H2O and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (EtOAc/hexanes=1:5)

출처 및 근거

ORD 기록
ord-a0299e06c2004f64b8275a606b3276f7
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08877747B2

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