Ethylene Glycol → 4-(4-tert-Butyl-phenyl)-indan-1-one

HRID 1169168노트

반응식

HRID 1169168 반응식
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].[C:12]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].C(O)CO.C(=O)([O-])[O-].[Na+].[Na+]>O.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=C(S([O-])(=O)=O)C=C(P(C2C=CC=C(S([O-])(=O)=O)C=2)C2C=CC=C(S([O-])(=O)=O)C=2)C=1.[Na+].[Na+].[Na+]>[C:12]([C:16]1[CH:21]=[CH:20][C:19]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH2:4][CH2:5][C:6]3=[O:11])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13]

참가 물질

8

반응물 4

HCID 174Ethylene GlycolHCID 10340Sodium CarbonateHCID 27343204-tert-Butylphenylboronic acidHCID 113326814-chloro-2,3-dihydro-1H-inden-1-one

생성물 1

HCID 229905194-(4-tert-Butyl-phenyl)-indan-1-one수율 96%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6099338Trisodium 3,3',3''-phosphinetriyltris(benzene-1-sulphonate)촉매HCID 962Water용매2회

실험 절차

14.0 g (84 mmol) of 4-chloroindanone, 32.9 g (185 mmol) of 4-tert-butylphenylboronic acid, 230 ml of ethylene glycol and 38 ml of water together with 19.6 g of sodium carbonate are placed in a reaction vessel and degassed three times. A solution of 94 mg (0.42 mmol) of Pd(OAc)2 and 2.1 ml (1.26 mmol) of TPPTS in 2 ml of water is subsequently added. The resulting reaction mixture is refluxed for 5 hours. After cooling, it is extracted three times with toluene and the combined organic phases are washed with saturated NaCl solution. After drying over magnesium sulfate, the solvent is removed in an oil pump vacuum. 21.3 g (96%) of the desired product are isolated.

후처리

  1. customdegassed three times
  2. customThe resulting reaction mixture
  3. temperatureis refluxed for 5 hours
  4. temperatureAfter cooling
  5. extractionit is extracted three times with toluene
  6. washthe combined organic phases are washed with saturated NaCl solution
  7. dry with materialAfter drying over magnesium sulfate
  8. customthe solvent is removed in an oil pump vacuum

출처 및 근거

ORD 기록
ord-e21b2a6e20df4519acd79ce1ea91338d
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06627764B1

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