Pyridine → 4-(Bis-decyl-carbamoyloxy)-undecanoic Acid hex-3-enyl Ester

HRID 1169183

Reaktionsgleichung

Reaktionsgleichung von HRID 1169183
[C:1](Cl)(Cl)=[O:2].[CH2:5]([O:11][C:12](=[O:24])[CH2:13][CH2:14][CH:15]([OH:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:6][CH:7]=[CH:8][CH2:9][CH3:10].N1C=CC=CC=1.[CH2:31]([NH:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>C1(C)C=CC=CC=1.O>[CH2:5]([O:11][C:12](=[O:24])[CH2:13][CH2:14][CH:15]([O:23][C:1](=[O:2])[N:41]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:6][CH:7]=[CH:8][CH2:9][CH3:10]

Komponenten

7

Edukt 4

HCID 1049Pyridine2×HCID 6371PhosgeneHCID 14261DidecylamineHCID 541528994-Hydroxy-undecanoic acid hex-3-enyl ester

Produkt 1

HCID 538307604-(Bis-decyl-carbamoyloxy)-undecanoic Acid hex-3-enyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To 6.20 ml of an ice-cooled 20% solution of phosgene in toluene was slowly added a solution of 3 g 4-hydroxy-undecanoic acid hex-3-enyl ester and 0.93 g pyridine in 3 ml toluene. The reaction mixture was stirred for 16 hours at room temperature. A mixture of 3.48 g didecylamine and 0.93 g pyridine was added and the mixture was stirred for another 16 hours. Water was added and the mixture extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, 2N hydrochloric acid, water, dried over magnesium sulfate and evaporated to dryness. The residue was chromatographed on silica gel to give 2.9 g of a colorless liquid.

Aufarbeitung

  1. additionwas added
  2. stirringthe mixture was stirred for another 16 hours
  3. extractionthe mixture extracted with ethyl acetate
  4. washThe organic layer was washed with saturated sodium bicarbonate, 2N hydrochloric acid, water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. customThe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-fb79587565a444369bf759f58078f671
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06627763B2

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