Sodium hydride → HCID 66577987, Verbindung

HRID 533562

Reaktionsgleichung

Reaktionsgleichung von HRID 533562
[H-].[Na+].[CH3:3][S:4]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:6])=[O:5].[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28]I)=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:27][CH2:28][CH:7]([S:4]([CH3:3])(=[O:6])=[O:5])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:25][CH:26]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 78201Ethyl methanesulfonylacetateHCID 104272231-((4-(2-Iodoethyl)phenoxy)methyl)benzene

Produkt 1

HCID 66577987HCID 66577987, VerbindungAusbeute 86,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (1.80 g, 45 mmol, 60% in mineral oil) was added in three portions to a solution of ethyl (methylsulfonyl)acetate (6.70 g, 40.3 mmol) in DMF (200 mL) at 0° C. The reaction was allowed to warm to room temperature and stirred for 1 hour. 1-(Benzyloxy)-4-(2-iodoethyl)benzene was added to the solution and the reaction was stirred overnight at rt. The reaction was quenched with 1N aqueous HCl (200 mL) and extracted with ethyl acetate (3×100 mL). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Chromatography on a Biotage 40 L column using 1:4 ethyl acetate in heptane afforded the title compound as a white solid (13.13 g, 86.5%). LC-MS m/z 375.2 (M−1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.34 (t, J=7.03 Hz, 3H) 2.31-2.47 (m, 2H) 2.55-2.68 (m, 1H) 2.70-2.80 (m, 1H) 3.00 (s, 3H) 3.66-3.80 (m, 1H) 4.18-4.38 (m, 2H) 5.06 (s, 2H) 6.92 (d, J=8.59 Hz, 2H) 7.09 (d, J=8.59 Hz, 2H) 7.31-7.47 (m, 5H).

Aufarbeitung

  1. stirringthe reaction was stirred overnight at rt
  2. customThe reaction was quenched with 1N aqueous HCl (200 mL)
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. dry with materialThe combined organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-82fc0e3c9d5141ae8ab2b14246b55db7
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853258B2

Verknüpfte Notizen

Wird geladen…