Toluene → 2-Phenyl-5-(prop-1-en-2-yl)pyridine

HRID 713559노트

반응식

HRID 713559 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][CH:7]=1.O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C:23]1(C)[CH:28]=CC=C[CH:24]=1.CC1(C)C(C)(C)OB(C(C)=C)O1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.O>[C:8]1([C:5]2[CH:4]=[CH:3][C:2]([C:23]([CH3:28])=[CH2:24])=[CH:7][N:6]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

8

반응물 4

HCID 1140TolueneHCID 27628665-Chloro-2-phenylpyridineHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 22031701Potassium phosphate, tribasic, monohydrate

생성물 1

HCID 866740462-Phenyl-5-(prop-1-en-2-yl)pyridine

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl촉매HCID 962Water용매

실험 절차

To a 1 L round bottom flask was added 5-chloro-2-phenylpyridine (10.15 g, 53.5 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (1.8 g, 4.3 mmol), potassium phosphate tribasic monohydrate (37.0 g, 161 mmol) with toluene (200 mL) and water (20 mL). The reaction mixture was degassed with nitrogen for 20 mins. 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (12.07 mL, 64.2 mmol) and Pd2(dba)3 (0.980 g, 1.070 mmol) were added and the reaction mixture was refluxed for 18 h. The aqueous layer was removed and the organic layer was concentrated to dryness. The crude product was chromatographed on silica gel with 0-20% EtOAc in hexane to yield 11 g of the desired product (HPLC purity: 95%). The product was confirmed by GC/MS.

후처리

  1. customThe reaction mixture was degassed with nitrogen for 20 mins
  2. temperaturethe reaction mixture was refluxed for 18 h
  3. customThe aqueous layer was removed
  4. concentrationthe organic layer was concentrated to dryness
  5. customThe crude product was chromatographed on silica gel with 0-20% EtOAc in hexane

출처 및 근거

ORD 기록
ord-f7f96cd5aaa44a039386603cc635eb86
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09184397B2

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