Triethylamine → Ethyl 3-(hexadecyloxy)-2-[(hexadecylthio)methyl]propanoate

HRID 248166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 248166
[CH2:1]([O:17][CH2:18][C:19](=[CH2:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(N(CC)CC)C.[CH2:33]([SH:49])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]>C(O)C>[CH2:1]([O:17][CH2:18][CH:19]([CH2:25][S:49][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 18015HexadecanethiolHCID 12971817Ethyl 2-[(hexadecyloxy)methyl]-2-propenoate

Produkt 1

HCID 19764340Ethyl 3-(hexadecyloxy)-2-[(hexadecylthio)methyl]propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 20 g of ethyl 2-[(hexadecyloxy)methyl]-2-propenoate in 60 ml of ethyl alcohol containing 10 ml of triethylamine is added 53 ml hexadecylmercaptan. Following stirring for 18 hours, the volatile components are removed and the residue is chromatographed by HPLC on silica gel using 9:1 hexanes:ethyl acetate. Fractions containing product are combined and the solvents evaporated to give 32.9 g of the desired product as a white waxy solid.

Aufarbeitung

  1. customthe volatile components are removed
  2. customthe residue is chromatographed by HPLC on silica gel using 9:1 hexanes
  3. additionFractions containing product
  4. customthe solvents evaporated

Quellen und Nachweise

ORD-Eintrag
ord-1a201f6298ac4d309631ce6847600db1
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05208223

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