1,2-Dimethoxyethane → 1-(2'-(Benzyloxy)-3'-phenylbiphenyl-3-yl)ethanone

HRID 45469노트

반응식

HRID 45469 반응식
FC(F)(F)S(O[C:7]1[C:8]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1)(=O)=O.[C:29]([C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1)(=[O:31])[CH3:30].C(COC)OC.C(=O)(O)[O-].[Na+]>O.[Pd].C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:20]([O:19][C:8]1[C:9]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:10][CH:11]=[CH:12][C:7]=1[C:36]1[CH:35]=[CH:34][CH:33]=[C:32]([C:29](=[O:31])[CH3:30])[CH:37]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

참가 물질

9

반응물 4

HCID 80711,2-DimethoxyethaneHCID 516892Sodium BicarbonateHCID 27343103-Acetylphenylboronic acidHCID 582385672-(Benzyloxy)biphenyl-3-yl trifluoromethanesulfonate

생성물 1

HCID 582385951-(2'-(Benzyloxy)-3'-phenylbiphenyl-3-yl)ethanone수율 100%

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 31 (3.18 g, 7.8 mmol), 3-acetylphenylboronic acid (1.6 g, 9.76 mmol, 1.25 equiv.), glyme (5 mL), bis(triphenylphosphine)palladium(II) dichloride (25 mg) and sodium bicarbonate (2.1 g) in water (40 mL) was kept at reflux under nitrogen for 11 hr with additional palladium catalyst (2×30 mg) added after 3 and 7 hr. After cooling, the reaction mixture was diluted with ethyl acetate (200 mL) and washed with water (2×800 mL). The organic layer was dried over sodium sulfate and filtered. The solvent was removed in a rotary evaporator and the crude product was purified by chromatography on silica (120 g) with 2% ethyl acetate in heptane (4 L) to afford 32 (2.9 g, 100%).

후처리

  1. additionadded after 3 and 7 hr
  2. temperatureAfter cooling
  3. washwashed with water (2×800 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed in a rotary evaporator
  7. customthe crude product was purified by chromatography on silica (120 g) with 2% ethyl acetate in heptane (4 L)

출처 및 근거

ORD 기록
ord-0f16a94773714b63b0a4c8cdcdc0b2f2
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541522B2

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