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Sodium hydride → 1-(5-Methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-6(2-fluorophenoxy)-hexan-1-one

HRID 620657
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 620657
[CH3:1][C:2]1([C:8](=[O:15])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[CH2:7][O:6][CH2:5][O:4][CH2:3]1.[H-].[Na+].Br[CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[F:30]>CN(C)C=O>[CH3:1][C:2]1([C:8](=[O:15])[CH:9]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[F:30])[CH2:7][O:6][CH2:5][O:4][CH2:3]1
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Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 71722941-(4-Bromobutoxy)-2-fluorobenzeneHCID 128556521-(5-Methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-ethan-1-one

Produkt 1

HCID 137154561-(5-Methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-6(2-fluorophenoxy)-hexan-1-oneAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
3×

Versuchsvorschrift

A solution of 42.2 g (0.2 mole) of 1-(5-methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-ethan-1-one in 150 ml of absolute dimethylformamide is added dropwise, at from 20° to 25° C., to a stirred suspension of 5.3 g (0.22 mole) of sodium hydride in 50 ml of absolute dimethylformamide, the suspension being kept under nitrogen. Stirring is continued for 3 hours, after which a solution of 49.4 g (0.2 mole) of 1-bromo-4-(2-fluorophenoxy)-butane in 50 ml of absolute dimethylformamide is added dropwise at 60° C. and the reaction mixture is then refluxed for a further 5 hours. About 100 ml of ice water are then carefully added dropwise at room temperature, and the mixture is extracted with three times 300 ml of methylene chloride. The organic phase is then washed several times with water, dried over Na2SO4 and evaporated down. Distillation (bp.=248° C./0.005) gives 56 g (74%) of 1-(5-methyl-1,3-dioxan-5-yl)-2-(1,2,4-triazol-1-yl)-6(2-fluorophenoxy)-hexan-1-one as a yellowish resin.

Aufarbeitung

  1. temperaturethe reaction mixture is then refluxed for a further 5 hours
  2. extractionthe mixture is extracted with three times 300 ml of methylene chloride
  3. washThe organic phase is then washed several times with water
  4. dry with materialdried over Na2SO4
  5. customevaporated down
  6. distillationDistillation (bp.=248° C./0.005)

Quellen und Nachweise

ORD-Eintrag
ord-ace80921aee84e0b98a65cdd87dfed91
Quelldatensatz
uspto-grants-1989_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04822400

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