Acetic Acid → 2-Decyloxy-5-(p-hydroxyphenyl)pyrimidine (+)-4-(1-hexyloxy-2,2,2-trifluoroethyl)benzoate

HRID 1728431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1728431
[CH2:1]([O:11][C:12]1[N:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)=[CH:14][N:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].N1(C2C=CN=CC=2)CCCC1.C1(N=C=NC2CCCCC2)CCCCC1.C(O)(=O)C.[CH2:55]([O:61][CH:62]([C:67]1[CH:75]=[CH:74][C:70]([C:71]([OH:73])=[O:72])=[CH:69][CH:68]=1)[C:63]([F:66])([F:65])[F:64])[CH2:56][CH2:57][CH2:58][CH2:59][CH3:60]>ClCCl>[CH2:55]([O:61][CH:62]([C:67]1[CH:75]=[CH:74][C:70]([C:71]([OH:73])=[O:72])=[CH:69][CH:68]=1)[C:63]([F:65])([F:66])[F:64])[CH2:56][CH2:57][CH2:58][CH2:59][CH3:60].[CH2:1]([O:11][C:12]1[N:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=2)=[CH:14][N:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 190180752-Decyloxy-5-(p-hydroxyphenyl)pyrimidineHCID 19018076(+)-4-(1-Hexyloxy-2,2,2-trifluoroethyl)benzoic acid

Produkt 1

HCID 867479682-Decyloxy-5-(p-hydroxyphenyl)pyrimidine (+)-4-(1-hexyloxy-2,2,2-trifluoroethyl)benzoateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In 20 ml of dry dichloromethane were dissolved 3.04 g of (10 millimoles) of optically active (+)-4-(1-hexyloxy-2,2,2-trifluoroethyl)benzoic acid, 3.28 g (10 millimoles) of 2-decyloxy-5-(p-hydroxyphenyl)pyrimidine and 0.2 g of 4-pyrrolidinopyridine. Then, 2.5 g (12 millimoles) of dicyclohexylcarbodiimide was added and the resulting mixture was stirred at room temperature for 6 hours. After the reaction, 5% aqueous solution of acetic acid was added and the whole was extracted with dichloromethane. The organic layer was washed successively with water and 7% aqueous solution of sodium hydrogen carbonate and dried on anhydrous magnesium sulfate, and then the solvent was distilled off and the residue was purified by silica gel column chromatography. Thus, 5.05 g (yield 82%) of optically active 2-decyloxy-5-(p-hydroxyphenyl)pyrimidine (+)-4-(1-hexyloxy-2,2,2-trifluoroethyl)benzoate was obtained.

Aufarbeitung

  1. additionwas added
  2. extractionthe whole was extracted with dichloromethane
  3. washThe organic layer was washed successively with water and 7% aqueous solution of sodium hydrogen carbonate
  4. dry with materialdried on anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d35929fba4e64311a6c72d1411ddc73f
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05326871

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