Dimethylamine → 2-(Dimethylamino)ethyl 5-(tetradecyloxy)furan-2-carboxylate

HRID 335537

Reaktionsgleichung

Reaktionsgleichung von HRID 335537
[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][CH2:24][CH2:25]Br)=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH3:27][NH:28][CH3:29]>C1COCC1>[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][CH2:24][CH2:25][N:28]([CH3:29])[CH3:27])=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Komponenten

4

Edukt 2

HCID 674DimethylamineHCID 498698992-Bromoethyl 5-(tetradecyloxy)furan-2-carboxylate

Produkt 1

HCID 498701652-(Dimethylamino)ethyl 5-(tetradecyloxy)furan-2-carboxylateAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 2-bromoethyl 5-(tetradecyloxy)furan-2-carboxylate (0.186 g, 0.43 mmol) (prepared in Example 5) in THF at 0° C. was added dimethylamine (1 mL of a 2M solution in THF, 2.15 mmol) with stirring. The solution was allowed to warm to room temperature and stirring was continued for 12 hrs at which time the reaction was concentrated to dryness. The crude material was purified by flash chromatography eluting with ethyl acetate in hexanes (5-35%) to yield 0.121 g (71%) of the title compound as a waxy, colourless solid. MS (m/z, ES+): 396.29 (M+1, 100%); 1H NMR (400 MHz, DMSO-d6) δ: 7.2 (d, 1H), 5.6 (d, 1H), 4.23 (t, 2H), 4.13 (t, 2H), 2.53 (t, 2H), 2.18 (s, 6H), 1.7 (p, 2H), 1.2-1.5 (m, 22H), 0.85 (t, 3H).

Aufarbeitung

  1. stirringstirring
  2. concentrationthe reaction was concentrated to dryness
  3. customThe crude material was purified by flash chromatography
  4. washeluting with ethyl acetate in hexanes (5-35%)

Quellen und Nachweise

ORD-Eintrag
ord-887bb610d8174f36a0850033d1a95458
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08884034B2

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