Sodium Carbonate → 2-Methyl-7-phenyl-1-indanone

HRID 2298466노트

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HRID 2298466 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)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>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.O>[CH3:12][CH:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:3]=[CH:4][CH:5]=2)[C:9]1=[O:11]

참가 물질

9

반응물 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 117898227-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one

생성물 1

HCID 185126012-Methyl-7-phenyl-1-indanone수율 94.5%

시약·촉매·용매 4

HCID 11776Triphenylphosphine촉매HCID 167845palladium(II) acetate촉매2회HCID 962Water용매2회HCID 7237O-Xylene용매

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온도
100 °C

실험 절차

2.5 g (13.8 mmol) of 7-chloro-2-methyl-1-indanone (1), 2.11 g (17.3 mmol) of phenylboronic acid and 3.66 g (34.6 mmol) of sodium carbonate were placed in 40 ml of o-xylene/5 ml of water 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 8 hours at 100° C. After 2, 4 and 6 hours, the same amount of palladium acetate and triphenylphosphine were added again each time. 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 2.9 g of (15) as solid. The 1H-NMR indicated a conversion of about 85%.

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-c74b003d0945420998f8bb9050e32d81
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06492539B1

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