Iodoethane → 2-(2,5-Dimethyl-pyrrol-1-yl)-6-propyl-pyridine

HRID 2197696ノート

反応式

HRID 2197696 の反応式
[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[Li+].[CH3:16][CH:17]([N-]C(C)C)C.C(I)C>C1COCC1>[CH3:7][C:4]1[N:3]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH2:16][CH3:17])[N:9]=2)[C:2]([CH3:1])=[CH:6][CH:5]=1

参加物

5

反応物 3

HCID 6340IodoethaneHCID 7931562-(2,5-Dimethyl-1H-pyrrol-1-yl)-6-methylpyridineHCID 2724682Lithium diisopropylamide

生成物 1

HCID 542277792-(2,5-Dimethyl-pyrrol-1-yl)-6-propyl-pyridine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-30 °C

実験手順

A solution of the product from Example 2a (7.53 g, 40.0 mmol) in 30 mL of dry THF was added dropwise with stirring to a solution of LDA (42.4 mmol) in 30 mL of dry THF at −30° C. Stirred at −30° C. for 30 min. Added EtI (3.42 mL, 42.0 mmol) in 20 mL of dry THF dropwise with stirring for 30 min then warmed to room temperature. After 2 h quenched by pouring into saturated NaCl solution and extracted with ether. Dried over MgSO4, filtered and concentrated under vacuum giving the title compound. The product was purified by silica gel column chromatography eluting with EtOAc/hexane to give the title compound (5.21 g, 60%).

後処理

  1. temperaturethen warmed to room temperature
  2. customAfter 2 h quenched
  3. additionby pouring into saturated NaCl solution
  4. extractionextracted with ether
  5. dry with materialDried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-54ccb51e2ba74ae58ac3698404a40e06
出典データセット
uspto-grants-2012_12
特許番号
US08338605B2

反応ノート

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