Toluene → 2-(5-Methyl-2-styrylphenyl)-pyridine

HRID 1510917ノート

反応式

HRID 1510917 の反応式
[C:1]1([CH3:13])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:2]=1.C(O[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=O)C.C1(C)C=CC=CC=1>CCN(CC)CC.CCOC(C)=O.CCCCCC>[CH3:13][C:1]1[CH:6]=[CH:5][C:4]([CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:3]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:2]=1

参加物

7

反応物 3

HCID 1140TolueneHCID 1145762-Phenylvinyl acetateHCID 27600142-(m-Tolyl)pyridine

生成物 1

HCID 689362712-(5-Methyl-2-styrylphenyl)-pyridine収率 98%

試薬・触媒・溶媒 3

HCID 8058Hexane溶媒HCID 8471Triethylamine溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

A Teflon-coated magnetic stirring rod was placed in a 10 mL two-necked flask which was then equipped with a reflux condenser. The reflux condenser was connected to a pressure reduced/nitrogen line and the whole apparatus was dried with heating under reduced pressure. Thereafter, N2 gas was charged in the reaction apparatus and the whole reaction apparatus was purged with nitrogen. The reaction vessel was left to cool to room temperature, then, Ru(cod)(cot) complex (0.05 mmol, 15.8 mg), 2-m-tolylpyridine (1 mmol, 169.2 mg), styryl acetate (3 mmol, 486.6 mg) and toluene (1.5 mL) were added. The mixture was heated by an oil bath and reacted under reflux condition for 50 hours. 50 hours after, the reaction solution was left to cool to room temperature, then, triethylamine (0.3 mL) was added. Isolation of the product was carried out by silica gel column chromatography (i.d.=30 mm; length=170-250 mm; hexane:EtOAc:Et3N=9:1:0.1; 25 mL each). A subject substance 2-(5-methyl-2-styrylphenyl)-pyridine was obtained with a yield of 98%.

後処理

  1. customwhich was then equipped with a reflux condenser
  2. customthe whole apparatus was dried
  3. temperaturewith heating under reduced pressure
  4. additionThereafter, N2 gas was charged in the reaction apparatus
  5. customthe whole reaction apparatus was purged with nitrogen
  6. waitThe reaction vessel was left
  7. temperatureThe mixture was heated by an oil bath
  8. customreacted
  9. temperatureunder reflux condition for 50 hours
  10. temperatureto cool to room temperature

出典と根拠

ORDレコード
ord-e1b1a56d6b8940f5b9fb0f406b3db7f4
出典データセット
uspto-grants-2012_07
特許番号
US08212048B2

反応ノート

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