Iodoethane → tert-butyl N-ethyl-N-(prop-2-yn-1-yl)carbamate

HRID 17171

Reaktionsgleichung

Reaktionsgleichung von HRID 17171
[H-].[Na+].[CH2:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[C:4]#[CH:5].[CH2:14](I)[CH3:15]>CN(C=O)C.O>[CH2:14]([N:6]([CH2:3][C:4]#[CH:5])[C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH3:15]

Komponenten

6

Edukt 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamate

Produkt 1

HCID 18366151tert-butyl N-ethyl-N-(prop-2-yn-1-yl)carbamateAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A suspension of sodium hydride (354 mg, 14.2 mmol) in DMF (33 mL) at room temperature was treated with a solution of Example 516A (2.0 g, 12.9 mmol) in DMF (10 mL) and stirred for one hour at room temperature. The solution was cooled to 0° C., treated with ethyl iodide (1.24 mL, 15.5 mmol), stirred for one hour at 0° and overnight at room temperature. The solution was diluted with water (25 mL), extracted with diethyl ether (2×50 mL) and the combined organic layers were washed with brine (30 mL0, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography on silica gel using 5-10% ethyl acetate/hexanes to give the 1.1 g (47% yield) of the desired product. MS (ESI(+)) m/e 184 (M+H)+.

Aufarbeitung

  1. temperatureThe solution was cooled to 0° C.
  2. stirringstirred for one hour at 0° and overnight at room temperature
  3. extractionextracted with diethyl ether (2×50 mL)
  4. washthe combined organic layers were washed with brine (30 mL0
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel using 5-10% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-093ae3d4bbe64e2187e00394a517fbec
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737160B2

Verknüpfte Notizen

Wird geladen…