1-Bromododecane → ethyl 1--N-dodecyl-2-pyrrolidone-5-carboxylate

HRID 2259174

Reaktionsgleichung

Reaktionsgleichung von HRID 2259174
[H-].[Na+].[NH:3]1[CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:5][C:4]1=[O:13].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C1COCC1>[CH2:26]([N:3]1[CH:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:5][C:4]1=[O:13])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15]

Komponenten

5

Edukt 3

HCID 89191-BromododecaneHCID 24758Sodium hydrideHCID 980475-Oxoproline ethyl ester

Produkt 1

HCID 19002573ethyl 1--N-dodecyl-2-pyrrolidone-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 1.92 g NaH (60%, washed with pet ether) in dry THF at room temperature under N2 was added dropwise a solution of 7.06 g of ethyl 2-pyrrolidone-5-carboxylate in 20 mL of THF. The mixture was refluxed for 1 h, cooled to room temperature, followed by dropwise addition of 1.3 equivalents of 1-bromododecane. After additional reflux overnight and workup, the crude oil was subjected to flash chromatography (silica, 8:2 pet ether/EtOAc) to give 3.14 g of ethyl 1--N-dodecyl-2-pyrrolidone-5-carboxylate as a clear oil: NMR (CDCl3) δ 4.2(m), 3.68(m), 2.9(m), 2.6-2.2(m), 2.1(m), 1.6-1.0(m), 0.9(t).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 1 h
  2. temperatureAfter additional reflux overnight

Quellen und Nachweise

ORD-Eintrag
ord-b7c1e72ec29c433f89fd5ef6c8a4bfeb
Quelldatensatz
uspto-grants-1995_12
Patentnummer
US05472946

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