1,2-Dichloroethane → N-methoxy-N-methylhept-6-enamide

HRID 1879244Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1879244
C(Cl)CCl.[C:5]([OH:13])(=O)[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[Cl-].[CH3:15][O:16][NH2+:17][CH3:18]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:15][O:16][N:17]([CH3:18])[C:5](=[O:13])[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11]

Komponenten

6

Edukt 3

HCID 111,2-DichloroethaneHCID 707056-Heptenoic acidHCID 11040634Methoxy(methyl)azanium;chloride

Produkt 1

HCID 46703846N-methoxy-N-methylhept-6-enamideAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

EDC (1.1 eq.) was added in small portions over 1.5 h to a stirred mixture of hept-6-enoic acid, methoxy(methyl)ammonium chloride (1.1 eq.) and DMAP (1.1 eq.) in CH2Cl2 (0.2 M). After 14 h, the mixture was diluted with CH2Cl2, then washed sequentially with hydrochloric acid (1 M), NaOH (1M), brine and dried (Na2SO4). Evaporation of the solvent afforded the title compound (97%) as a colorless oil. 1H NMR (400 MHz, CDCl3, 300 K) δ 5.87-5.75 (m, 1H), 5.01 (d, J 17.1, 1H), 4.95 (d, J 10.1, 1H), 3.68 (s, 3H), 3.18 (s, 3H), 2.48-2.36 (m, 2H), 2.13-2.04 (m, 2H), 1.71-1.60 (m, 2H), 1.50-1.40 (m, 2H).

Aufarbeitung

  1. washwashed sequentially with hydrochloric acid (1 M), NaOH (1M), brine
  2. dry with materialdried (Na2SO4)
  3. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-3793365b54694eabbd614a7081c47ada
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314062B2

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