Acetic Acid → HCID 178446993, Verbindung

HRID 1742771

Reaktionsgleichung

Reaktionsgleichung von HRID 1742771
C([Li])CCC.C(NC(C)C)(C)C.[Cl-].[Cl-].[CH-:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.[CH-:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1.[Ti+2:25].[Cl:26][C:27]1[CH:32]=[C:31]([O:33][CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[N:30]=[C:29]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:28]=1.[C:45]([OH:48])(=[O:47])[CH3:46]>O1CCCC1.O>[CH:15]1([Ti:25]([CH:20]2[CH:24]=[CH:23][CH:22]=[CH:21]2)[O:47][C:45](=[O:48])[CH2:46][C:32]2[C:27]([Cl:26])=[N:28][C:29]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[N:30][C:31]=2[O:33][CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[CH:19]=[CH:18][CH:17]=[CH:16]1

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 7912DiisopropylamineHCID 190067994-Chloro-6-(3-methylbut-1-oxy)-2-phenylpyrimidineHCID 124040768Titanocene dichiorideHCID 178418339Butyllithium

Produkt 1

HCID 178446993HCID 178446993, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

69 ml (0.11 mol, 1.6M) of butyllithium are added dropwise over the course of 15 minutes under a nitrogen atmosphere to a solution of 15.6 ml (0.11 mol) of diisopropylamine in 200 ml of tetrahydrofuran at 0° C. This solution is added dropwise at from -70° to -60° C. over the course of 2 hours to a suspension of 24.9 g (0.1 mol) of titanocene dichloride and 27.7 g (0.1 mol) of 4-chloro-6-(3-methylbut-1-oxy)-2-phenylpyrimidine in 1000 ml of tetrahydrofuran. The reaction mixture is stirred at -70° C. for 1 hour, allowed to warm to room temperature over the course of about 3 hours and then poured, with stirring, into water and 19.0 g (0.23 mol) of acetic acid. The resultant red-orange emulsion is filtered through ®Hyflo. The organic phase is separated off, dried using magnesium sulfate, filtered and evaporated on a rotary evaporator. The residue is purified by flash chromatography with hexane:ethyl acetate in the ratio 3:1 as eluent, giving 11.2 g (22.4% of theory) of the title compound as a yellow powder having a melting point of 158° C.

Aufarbeitung

  1. temperatureto warm to room temperature over the course of about 3 hours
  2. additionpoured
  3. filtrationThe resultant red-orange emulsion is filtered through ®Hyflo
  4. customThe organic phase is separated off
  5. customdried
  6. filtrationfiltered
  7. customevaporated on a rotary evaporator
  8. customThe residue is purified by flash chromatography with hexane

Quellen und Nachweise

ORD-Eintrag
ord-12502a90446245439539eafe2e1e56e7
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05340701

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