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Water → HCID 19756351, Verbindung

HRID 1587826
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1587826
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH2:10][O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:6][CH:7]=1.[C:29]([CH2:33][C:34](OC)=[O:35])(=O)[CH2:30][CH3:31].O>C1CCCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Si:12]([O:11][CH2:10][CH2:9][O:8][C:5]1[N:6]=[C:7]2[C:2](=[CH:3][CH:4]=1)[NH:1][C:29]([CH2:30][CH3:31])=[CH:33][C:34]2=[O:35])([C:25]([CH3:28])([CH3:27])[CH3:26])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 962WaterHCID 121699Methyl 3-oxovalerateHCID 19756412HCID 19756412, Verbindung

Produkt 1

HCID 19756351HCID 19756351, VerbindungAusbeute 51,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6101p-Toluenesulfonic acidKatalysator
HCID 8078
Cyclohexane
Lösungsmittel

Reaktionsbedingungen

Temperatur
260 °C

Versuchsvorschrift

A solution of compound C (89.5 g), methyl propionylacetate (32.8 g) and p-toluenesulphonic acid (1.0 g) in cyclohexane (900 ml) was heated under reflux with azeotropic removal of water for 20 hours. Volatile material was then removed from the reaction mixture by evaporation and the residue was dissolved in ethyl acetate (1 l). The solution was washed with saturated sodium hydrogen carbonate solution (500 ml), water (500 ml), saturated sodium chloride solution (500 ml), and then dried (MgSO4). The solvent was removed by evaporation and the residue dissolved in a eutectic mixture of 26.5% v/v diphenyl and 73.5% v/v diphenyl oxide (750 ml). The solution was heated to 260° C. and the temperature maintained for 30 minutes. The solution was cooled and diluted with hexane (1 l) to give 6-[2-(t-butyldiphenylsilyl)oxyethoxy]-2-ethyl-1,5-naphthyridin-4(1H)-one (D) (55.4 g), as a white solid, m.p. 209°-210° C.; NMR (d6 -DMSO): 1.1(s,9H), 1.35(t,3H), 2.8(q,2H), 4.15(t,2H), 4.65(t,2H), 6.3(br s,1H), 7.25(d,1H), 7.5-7.6(m,7H), 7.65-7.8(m,4H), 8.1(d,1H).

Aufarbeitung

  1. customVolatile material was then removed from the reaction mixture by evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate (1 l)
  3. washThe solution was washed with saturated sodium hydrogen carbonate solution (500 ml), water (500 ml), saturated sodium chloride solution (500 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed by evaporation
  6. dissolutionthe residue dissolved in a eutectic mixture of 26.5% v/v diphenyl and 73.5% v/v diphenyl oxide (750 ml)
  7. temperaturethe temperature maintained for 30 minutes
  8. temperatureThe solution was cooled
  9. additiondiluted with hexane (1 l)

Quellen und Nachweise

ORD-Eintrag
ord-c6a335c15aa345fbbb468bf74837cc62
Quelldatensatz
uspto-grants-1993_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05219863

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