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

HRID 646253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 646253
[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-e5ac1c5f2e3045679f5546edb5dc95d7
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705030B2

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