Ethylene Glycol → 2-methyl-4-phenyl-2,3,6,7-tetrahydro-s-indacen-1(5H)-one

HRID 271794

반응식

HRID 271794 반응식
Br[C:2]1[C:13]2[CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH3:15])[C:6]2=[O:14].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)CO>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.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:16]1([C:2]2[C:13]3[CH2:12][CH2:11][CH2:10][C:9]=3[CH:8]=[C:7]3[C:3]=2[CH2:4][CH:5]([CH3:15])[C:6]3=[O:14])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

참가 물질

8

반응물 4

HCID 174Ethylene GlycolHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 235470494-Bromo-2-methyl-2,3,6,7-tetrahydro-s-indacen-1(5H)-one

생성물 1

HCID 235470482-methyl-4-phenyl-2,3,6,7-tetrahydro-s-indacen-1(5H)-one수율 97.1%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6099338Trisodium 3,3',3''-phosphinetriyltris(benzene-1-sulphonate)촉매HCID 962Water용매3회

반응 조건

온도
80 °C

실험 절차

10 g (37.7 mmol) of 4-Bromo-2-methyl-3,5,6,7-tetrahydro-s-indacen-1(2H)-one (1b), 5.5 g (45.3 mmol) of phenylboronic acid, 8.8 g (80 mmol) of sodium carbonate, 80 ml of ethylene glycol and 12 ml of water were placed under a protective argon atmosphere and heated to 80° C. While stirring vigorously freshly prepared catalyst solution of 20 mg of palladium (II) acetate, 260 mg of 3,3′,3″-phoshinidynetris(benzenesulfonic acid)trisodium salt (TPPTS) in 4 ml of water were added to the reaction and the reaction mixture was refluxed for 3 hrs. After cooling to room temperature, 40 ml of water was added and the ethylene glycol phase was extracted three times with a total of 240 ml of toluene. The combined organic phases were washed twice with a total of 250 ml of aqueous sodium chloride and dried over 150 g of sodium sulfate. Removal of solvents gave 9.6 g of brawn oil, which was gradually crystallized (97%, GC-MS).

후처리

  1. additionwere added to the reaction
  2. temperaturethe reaction mixture was refluxed for 3 hrs
  3. temperatureAfter cooling to room temperature
  4. extractionthe ethylene glycol phase was extracted three times with a total of 240 ml of toluene
  5. washThe combined organic phases were washed twice with a total of 250 ml of aqueous sodium chloride
  6. dry with materialdried over 150 g of sodium sulfate
  7. customRemoval of solvents

출처 및 근거

ORD 기록
ord-ecfffcfd84fc4717965101b595918aab
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452949B2

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