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

HRID 713559ノート

反応式

HRID 713559 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl触媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f7f96cd5aaa44a039386603cc635eb86
出典データセット
uspto-grants-2015_11
特許番号
US09184397B2

反応ノート

読み込み中…