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

HRID 1646076

반응식

HRID 1646076 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 189389212-Pentyl-5-(t-butylsulfonamido)thiophene수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-20 °C

실험 절차

To a solution of 2-(t-butylsulfonamido)thiophene (3.42 g, 15.6 mmol) in anhydrous THF coole 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 additional 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). 1H NMR (200 MHz, CDCl 3) δ0.91 (t, 3H), 1.28 (s, 9H), 1.33 (m, 4H), 1.68 (bt, 2H), 2.81 (t, 2H), 4.63 (s, 1H), 6.69 (d, 1H), 7.41 (d, 1H).

후처리

  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

출처 및 근거

ORD 기록
ord-1a0958bfa93e477a857dcb12c78f2fb0
출처 데이터셋
uspto-grants-1993_01
특허 번호
US05177074

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