Butyric Acid → N-Methoxy-N-methylbutyramide

HRID 40905

Reaktionsgleichung

Reaktionsgleichung von HRID 40905
[C:1]([OH:6])(=O)[CH2:2][CH2:3][CH3:4].Cl.[CH3:8][NH:9][O:10][CH3:11].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[CH3:11][O:10][N:9]([CH3:8])[C:1](=[O:6])[CH2:2][CH2:3][CH3:4]

Komponenten

5

Edukt 3

HCID 264Butyric AcidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Produkt 1

HCID 13704543N-Methoxy-N-methylbutyramideAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of butanoic acid (1.01 g, 0.0115 mol) and N,O-dimethylhydroxylamine hydrochloride (1.12 g, 0.0115 mol) in DCM (50 mL) was added benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate (5.6 g, 0.013 mol) and TEA (3.2 mL, 0.023 mol). The mixture was stirred overnight at room temperature. The solution was then washed with water and brine, dried over sodium sulfate, and concentrated in vacuo. The crude product was purified by flash column chromatography (ether/hexanes). The solvent was removed (235 mbar/40° C.) to afford the product (1.33 g, 88%). 1H NMR (300 MHz, CDCl3): δ □3.68 (s, 3H), 3.18 (s, 3H), 2.40 (t, 2H), 1.74-1.59 (m, 2H), 0.96 (t, 3H).

Aufarbeitung

  1. washThe solution was then washed with water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash column chromatography (ether/hexanes)
  5. customThe solvent was removed (235 mbar/40° C.)

Quellen und Nachweise

ORD-Eintrag
ord-422690503fe34e8f85feb6f1a48e40d8
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530485B2

Verknüpfte Notizen

Wird geladen…