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4-Penten-1-OL → 2-[4-(5-Hydroxy-1-pentenyl)phenyl]-5-(ethoxy)pyrimidine

HRID 1728263
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1728263
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH2:17]([OH:22])[CH2:18][CH2:19][CH:20]=[CH2:21].C(=O)(O)[O-].[Na+].CN1CCCC1=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[OH:22][CH2:17][CH2:18][CH2:19][CH:20]=[CH:21][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][N:9]=2)=[CH:4][CH:3]=1
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Komponenten

8

Edukt 4

HCID 131814-Penten-1-OLHCID 13387N-methyl-2-pyrrolidoneHCID 516892Sodium BicarbonateHCID 190171162-(4-Bromophenyl)-5-ethoxypyrimidine

Produkt 1

HCID 540063702-[4-(5-Hydroxy-1-pentenyl)phenyl]-5-(ethoxy)pyrimidineAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11776
Triphenylphosphine
Katalysator
HCID 167845palladium(II) acetateKatalysator
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 14.7 g of 2-(4-bromophenyl)-5-(ethoxy)-pyrimidine, 5.7 g of 4-penten-1-ol, 10 g of sodium bicarbonate and 20 ml of N-methylpyrrolidone was treated with 0.3 g of triphenylphosphine and 0.12 g of palladium acetate. The reaction mixture was heated at 120° C. for 2 hours under a nitrogen atmosphere, then poured into 100 ml of water and extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed twice with 100 ml of concentrated sodium chloride solution each time, dried over magnesium sulfate, filtered and subsequently concentrated. Chromatography of the residue on silica gel with hexane/ethyl acetate (vol. 8:2) and recrystallization from ethyl alcohol gave 12 g of 2-[4-(5-hydroxy-1-pentenyl)phenyl]-5-(ethoxy)pyrimidine.

Aufarbeitung

  1. extractionextracted three times with 50 ml of diethyl ether each time
  2. washThe combined organic phases were washed twice with 100 ml of concentrated sodium chloride solution each time
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationsubsequently concentrated
  6. customChromatography of the residue on silica gel with hexane/ethyl acetate (vol. 8:2) and recrystallization from ethyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-d4da905fb90343e6a579231fa0f5ca90
Quelldatensatz
uspto-grants-1994_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05326497

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