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

HRID 1728429
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Reaktionsgleichung

Reaktionsgleichung von HRID 1728429
[CH2:1]([O:9][C:10]1[CH:11]=[N:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[N:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].N1(C2C=CN=CC=2)CCCC1.C1(N=C=NC2CCCCC2)CCCCC1.C(O)(=O)C.[CH2:53]([O:59][CH:60]([C:65]1[CH:73]=[CH:72][C:68]([C:69]([OH:71])=[O:70])=[CH:67][CH:66]=1)[C:61]([F:64])([F:63])[F:62])[CH2:54][CH2:55][CH2:56][CH2:57][CH3:58]>ClCCl>[CH2:53]([O:59][CH:60]([C:65]1[CH:73]=[CH:72][C:68]([C:69]([OH:71])=[O:70])=[CH:67][CH:66]=1)[C:61]([F:63])([F:64])[F:62])[CH2:54][CH2:55][CH2:56][CH2:57][CH3:58].[CH2:1]([O:9][C:10]1[CH:15]=[N:14][C:13]([C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)=[N:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 19018076(+)-4-(1-Hexyloxy-2,2,2-trifluoroethyl)benzoic acidHCID 135708811Phenol, 4-[5-(octyloxy)-2-pyrimidinyl]-

Produkt 1

HCID 136378407
5-Octyloxy-2-(p-hydroxyphenyl)pyrimidine (+)-4-(1-hexyloxy-2,2,2-trifluoroethyl)benzoate
Ausbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In 20 ml of dry dichloromethane were dissolved 3.04 g (10 millimoles) of optically active (+)-4-(1-hexyloxy-2,2,2-trifluoroethyl)benzoic acid, 3.00 g (10 millimoles) of 5-octyloxy-2-(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, 4.75 g (yield 81%) of optically active 5-octyloxy-2-(p-hydroxyphenyl)pyrimidine (+)-4-(1-hexyloxy-2,2,2-trifluoroethyl)benzoate was obtained. ##STR8##

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-f2408dd5f5954a3eac469637d10d8039
Quelldatensatz
uspto-grants-1994_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05326871

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