1-Iodopentane → 2-Pentyl-5-(t-butylsulfonamido)thiophene

HRID 1656122

反応式

HRID 1656122 の反応式
[C:1]([S:5]([NH:8][C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.I[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C1COCC1>[CH2:20]([C:11]1[S:10][C:9]([NH:8][S:5]([C:1]([CH3:4])([CH3:2])[CH3:3])(=[O:7])=[O:6])=[CH:13][CH:12]=1)[CH2:21][CH2:22][CH2:23][CH3:24]

参加物

5

反応物 3

HCID 123351-IodopentaneHCID 197896552-(t-Butylsulfonamido)thiopheneHCID 178418339Butyllithium

生成物 1

HCID 189389212-Pentyl-5-(t-butylsulfonamido)thiophene収率 60%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

To a solution of 2-(t-butylsulfonamido)thiophene (3.42 g, 15.6 mmol) in anhydrous THF cooled to -78° C. under N2 was added 2.5M n-BuLi (15.6 mL, 2.5 equiv). The reaction was warmed to -20° C. over 3.5 h. After stirring at -20° C. for an addional h, iodopentane (2.4 mL, 1.2 equiv) was added. The ice bath was removed and the reaction was stirred at rt overnight. The next day the reaction was quenched with sat'd NH4Cl solution and the THF was removed in vacuo. The residue was extracted with Et2O/EtOAc and washed with water and brine. The organic was dried over anhydrous MgSO4 and concentrated in vacuo. The product was purified by flash chromatography on a silica column eluting with Hex/EtOAc (15:1). Removal of the solvent afforded 2.72 g (60%) of the titled compound as a yellow oil. Rf=0.4 (6:1 Hex/EtOAc).

後処理

  1. additionwas added
  2. customThe ice bath was removed
  3. customThe next day the reaction was quenched with sat'd NH4Cl solution
  4. customthe THF was removed in vacuo
  5. extractionThe residue was extracted with Et2O/EtOAc
  6. washwashed with water and brine
  7. dry with materialThe organic was dried over anhydrous MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe product was purified by flash chromatography on a silica column
  10. washeluting with Hex/EtOAc (15:1)
  11. customRemoval of the solvent

出典と根拠

ORDレコード
ord-06b1251e0631498d98279cd9bc00e27f
出典データセット
uspto-grants-1993_10
特許番号
US05252574

関連ノート

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