4-Methyl-2,3,5,6-tetrafluorobenzyl alcohol → 2,3,5,6-tetrafluoro-4-methylbenzyl (RS)-2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-3,3-dimethylbutanoate

HRID 1088313

Reaktionsgleichung

Reaktionsgleichung von HRID 1088313
[CH3:1][C:2]([C:5]1[N:10]=[CH:9][C:8]([CH:11]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][N:6]=1)([CH3:4])[CH3:3].[F:21][C:22]1[C:29]([F:30])=C(C)[C:27]([F:32])=[C:26]([F:33])[C:23]=1[CH2:24]O>[Ti].C1(C)C=CC=CC=1>[CH3:4][C:2]([C:5]1[N:6]=[CH:7][C:8]([CH:11]([C:17]([CH3:19])([CH3:18])[CH3:20])[C:12]([O:14][CH2:15][C:16]2[C:29]([F:30])=[C:22]([F:21])[C:23]([CH3:24])=[C:26]([F:33])[C:27]=2[F:32])=[O:13])=[CH:9][N:10]=1)([CH3:1])[CH3:3]

Komponenten

5

Edukt 2

HCID 27342094-Methyl-2,3,5,6-tetrafluorobenzyl alcoholHCID 14718703ethyl (RS)-2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-3,3-dimethylbutanoate

Produkt 1

HCID 147188642,3,5,6-tetrafluoro-4-methylbenzyl (RS)-2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-3,3-dimethylbutanoateAusbeute 46,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23963TitaniumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of ethyl (RS)-2-[2-(1,1-dimethylethyl)pyrimidin-5-yl]-3,3-dimethylbutanoate (0.07 g), 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (0.1 g), titanium IV ethoxide (catalytic amount) and dry toluene (2 cm3) was heated at the reflux temperature for 10 hours. After cooling, the solvent was evaporated under reduced pressure to leave a brown gum, which was purified by preparative thin layer chromatography on 20 cm×20 cm×0.2 cm silica gel plates, eluting with dichloromethane containing 2% by volume ethyl acetate, to give the title compound (0.05 g) as an oil which solidified on standing.

Aufarbeitung

  1. temperaturewas heated at the reflux temperature for 10 hours
  2. temperatureAfter cooling
  3. customthe solvent was evaporated under reduced pressure
  4. customto leave a brown gum, which
  5. customwas purified by preparative thin layer chromatography on 20 cm×20 cm×0.2 cm silica gel plates
  6. washeluting with dichloromethane containing 2% by volume ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-491d0188b03a433490061091862b5c7e
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04962109

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