Water → HCID 22173111, 화합물

HRID 2298470노트

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HRID 2298470 반응식
Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[CH:8]([CH3:12])[CH2:7]2.[C:13]1(B(O)O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC1C=CC=CC=1C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:12][CH:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:21]3[C:22]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:18]=[CH:19][CH:20]=3)[CH:3]=[CH:4][CH:5]=2)[C:9]1=[O:11]

참가 물질

9

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 117898227-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one

생성물 1

HCID 22173111HCID 22173111, 화합물수율 89.9%

시약·촉매·용매 4

HCID 11776Triphenylphosphine촉매HCID 74236Tetrabutylammonium Bromide촉매HCID 167845palladium(II) acetate촉매HCID 7237O-Xylene용매

반응 조건

온도
125 °C

실험 절차

2.5 g (13.8 mmol) of 7-chloro-2-methyl-1-indanone (1), 2.86 g (16.6 mmol) of naphthylboronic acid, 0.22 g (0.68 mmol) of tetrabutylammonium bromide and 3.66 g (34.6 mmol) of sodium carbonate were placed in 40 ml of o-xylene in the reaction vessel, the mixture was degassed a number of times and saturated with argon. After addition of 1.55 mg (0.0069 mmol) of palladium acetate and 7.3 mg (0.027 mmol) of triphenylphosphine, the reaction mixture was stirred for 9 hours at 125° C. After addition of 40 ml of water, the phases were separated, the aqueous phase was extracted 3 times with 40 ml each time of ether, the combined organic phases were washed with 40 ml of water and 40 ml of saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent gave 3.38 g of (16) as solid.

후처리

  1. customthe mixture was degassed a number of times
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted 3 times with 40 ml each time of ether
  4. washthe combined organic phases were washed with 40 ml of water and 40 ml of saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of the solvent

출처 및 근거

ORD 기록
ord-6ddf955ea9b942268bf255ef1e022bf7
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06492539B1

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