Lauric Acid → (+)-2-{4-(1-Dodecanoyloxyethyl)phenyl}-5-decyloxypyrimidine

HRID 274179

Reaktionsgleichung

Reaktionsgleichung von HRID 274179
[OH:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:12][N:11]=2)=[CH:6][CH:5]=1)[CH3:3].[C:27](O)(=[O:39])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>ClCCl>[C:27]([O:1][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:12][N:11]=2)=[CH:8][CH:9]=1)[CH3:3])(=[O:39])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Komponenten

6

Edukt 4

HCID 3893Lauric AcidHCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 214682802-(4-(1-Hydroxyethyl)phenyl)-5-decyloxypyrimidine

Produkt 1

HCID 21468295(+)-2-{4-(1-Dodecanoyloxyethyl)phenyl}-5-decyloxypyrimidineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Into 20 ml of dichloromethane were dissolved 1.78 g (5 millimoles) of the (+)-2-{4-(1-hydroxyethyl)phenyl}-5-decyloxypyrimidine obtained in Preparation Example [starting material compound (VI)]70 and 1.2 g (6 millimoles) of dodecanic acid, and then 1.4 g of N,N'-dicyclohexylcarbodiimide and 0.1 g of 4-pyrrolidinopyridine were added thereto, followed by stirring at room temperature for 24 hours. After completion of the reaction, the precipitates were filtered off and 200 ml of toluene were added thereto, followed by washing with water, 5% acetic acid, water, 5% aqueous sodium hydrogen carbonate solution and water in this order. After the organic phase was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; toluene:ethyl acetate) to obtain 2.53 g (yield: 94%) of (+)-2-{4-(1-dodecanoyloxyethyl)phenyl}-5-decyloxypyrimidine. The physical values are shown in Table-1.

Aufarbeitung

  1. customAfter completion of the reaction
  2. filtrationthe precipitates were filtered off
  3. addition200 ml of toluene were added
  4. washby washing with water, 5% acetic acid, water, 5% aqueous sodium hydrogen carbonate solution and water in this order
  5. dry with materialAfter the organic phase was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent; toluene:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2026f0e84e994620be221f3c645de7d2
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389293

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