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Cesium fluoride → 2-(3,5-Dimethylbiphenyl-4-yl)-3-methoxy cyclopent-2-enone

HRID 509161
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HRID 509161 반응식
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:10](=[O:16])[CH2:11][CH2:12][C:13]=2[O:14][CH3:15])=[C:4]([CH3:17])[CH:3]=1.[F-].[Cs+].[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:17][C:4]1[CH:3]=[C:2]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=[C:6]([CH3:8])[C:5]=1[C:9]1[C:10](=[O:16])[CH2:11][CH2:12][C:13]=1[O:14][CH3:15]
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참가 물질

5

반응물 3

HCID 25953Cesium fluorideHCID 66827Phenylboronic AcidHCID 668681542-(4-Bromo-2,6-dimethylphenyl)-3-methoxy-cyclopent-2-enone

생성물 1

HCID 584815132-(3,5-Dimethylbiphenyl-4-yl)-3-methoxy cyclopent-2-enone수율 70.4%

시약·촉매·용매 1

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매

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온도
80 °C

실험 절차

To a mixture of 2-(4-bromo-2,6-dimethylphenyl)-3-methoxy-cyclopent-2-enone (1 g, 3.4 mmol), cesium fluoride (1.5 g, 9.87 mmol), phenylboronic acid (0.5 g, 4.1 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) (0.44 g, 0.54 mmol) is added degassed dimethoxyethane (10 ml) and the resulting suspension is stirred under nitrogen for 45 minutes then heated at 80° C. for 4 hrs. After cooling to room temperature the reaction mixture is acidified with 1N aqueous hydrochloric acid. The aqueous phase is further extracted with ethyl acetate (3×100 ml) and then all organic fractions are combined, dried over anhydrous sodium sulphate and concentrated in vacuo. The resulting material is purified by column chromatography on silica gel to afford 2-(3,5-dimethylbiphenyl-4-yl)-3-methoxy cyclopent-2-enone (0.7 g) as a white solid.

후처리

  1. additionis added
  2. customdegassed dimethoxyethane (10 ml)
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. extractionThe aqueous phase is further extracted with ethyl acetate (3×100 ml)
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe resulting material is purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-38dda0816c77469e87ef0383e8fbc78f
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09096560B2

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