1-Bromo-2-methylpropane → HCID 86702131, Verbindung

HRID 1776182Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1776182
[H-].[Na+].[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][NH:9][S:10]([CH3:13])(=[O:12])=[O:11].Br[CH2:15][CH:16]([CH3:18])[CH3:17]>CN(C)C=O.C(OCC)(=O)C>[O:3]1[CH:7]=[CH:6][CH:5]=[C:4]1[CH2:8][N:9]([CH2:17][C:16]([CH3:18])=[CH2:15])[S:10]([CH3:13])(=[O:12])=[O:11]

Komponenten

6

Edukt 3

HCID 65551-Bromo-2-methylpropaneHCID 24758Sodium hydrideHCID 240162N-(furan-2-ylmethyl)methanesulfonamide

Produkt 1

HCID 86702131HCID 86702131, VerbindungAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sodium hydride (60% mineral oil dispersion, 0.284 g, 7.1 mmol) was added in portions to a stirring solution of N-(furan-2-ylmethyl)methanesulfonamide (1.0 g, 5.7 mmol) in anhydrous N,N-dimethylformamide (12 mL), which was kept at 0° C. by an external ice bath. The ice bath was removed and the mixture was stirred for 50 mins at ambient temperature. 3-bromo-2-methylpropane (1.15 g, 8.6 mmol) was added in one portion, and the resulting mixture was stirred overnight at 65° C. before being diluted with ethyl acetate. The organic layer was successively washed with water and saturated aqueous sodium chloride solutions, dried (anhydrous sodium sulfate), filtered, and concentrated. The crude material was purified by silica gel column chromatography (0-50% ethyl acetate in hexanes) to give a clear liquid (1.24 g, 95%). 1H NMR (CDCl3, 300 MHz) δ 7.41-7.40 (m, 1H), 6.38-6.34 (m, 1H), 6.29-6.28 (m, 1H), 5.03-5.00 (m, 2H), 4.37 (s, 2H), 3.73 (s, 2H), 2.76 (s, 3H), 1.77 (s, 3H).

Aufarbeitung

  1. customwas kept at 0° C. by an external ice bath
  2. customThe ice bath was removed
  3. stirringthe resulting mixture was stirred overnight at 65° C.
  4. washThe organic layer was successively washed with water and saturated aqueous sodium chloride solutions
  5. dry with materialdried (anhydrous sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified by silica gel column chromatography (0-50% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1c0706801581426885fdc06e0a90edc4
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09265772B2

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