Iodoethane → 1-Ethyl-4-iodo-2-methanesulfonyl-1H-pyrrole

HRID 2220470Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2220470
[I:1][C:2]1[CH:3]=[C:4]([S:7]([CH3:10])(=[O:9])=[O:8])[NH:5][CH:6]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:17](I)[CH3:18]>CN(C=O)C.CCOC(C)=O>[CH2:17]([N:5]1[CH:6]=[C:2]([I:1])[CH:3]=[C:4]1[S:7]([CH3:10])(=[O:9])=[O:8])[CH3:18]

Komponenten

6

Edukt 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 597726954-iodo-2-methanesulfonyl-1H-pyrrole

Produkt 1

HCID 597727121-Ethyl-4-iodo-2-methanesulfonyl-1H-pyrroleAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 4-iodo-2-methanesulfonyl-1H-pyrrole (0.14 g, 0.52 mmol) in DMF was treated with Cs2CO3 (0.84 g, 2.58 mmol) and ethyl iodide (0.161 g, 1.03 mmol). The reaction mixture was diluted with EtOAc and washed sequentially with water and brine. The organic phase was separated, dried (Na2SO4) and concentrated in vacuo. Chromatography of the resultant residue (silica gel, 10%-30% EtOAc-hexanes as eluent) yielded an oil; 1H NMR (400 MHz, CDCl3) δ: 1.47 (t, 3H, J=7.3 Hz), 3.09 (s, 3H), 4.26 (q, 2H, J=7.3 Hz), 6.90 (m, 1H), 6.95 (s, 1H).

Aufarbeitung

  1. washwashed sequentially with water and brine
  2. customThe organic phase was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ade7447284d349bebb795c3e66dd894d
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07417047B2

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