Sodium hydride → 1-(1H-1,2,4-triazol-1-yl)-2-(4-chlorophenoxymethyl)-3,3-dimethylbutene

HRID 615067

Reaktionsgleichung

Reaktionsgleichung von HRID 615067
[H-].[Na+].[N:3]1([CH2:8]P(=O)(OCC)OCC)[CH:7]=[N:6][CH:5]=[N:4]1.[CH3:17][C:18]([CH3:31])([C:20](=O)[CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[CH3:19].C1OCCOCCOCCOCCOC1>C(COC)OC>[N:3]1([CH:8]=[C:20]([CH2:21][O:22][C:23]2[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=2)[C:18]([CH3:31])([CH3:17])[CH3:19])[CH:7]=[N:6][CH:5]=[N:4]1

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 905182-Butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-HCID 15145771Diethyl [(1H-1,2,4-triazol-1-yl)methyl]phosphonate

Produkt 1

HCID 543931591-(1H-1,2,4-triazol-1-yl)-2-(4-chlorophenoxymethyl)-3,3-dimethylbutene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel2×

Versuchsvorschrift

15 g of sodium hydride in the form of a 55% dispersion in oil are added under nitrogen to 150 ml of 1,2-dimethoxyethane. Then a solution of 69 g (0.315 mole) of diethyl (1H-1,2,4-triazol-1-yl)methylphosphonate, 68 g (0.3 mole) of 2,2-dimethyl-4-(4-chlorophenoxy)butan-3-one and a trace of 15-crown-5 in 500 ml of dimethoxyethane are added dropwise. The reaction mixture is stirred for about 10 hours and, after the dropwise addition of ice/water, extracted with methylene chloride. The combined extracts are washed with water, dried over sodium sulfate, filtered and concentrated. The oily residue is purified by column chromatography over silica gel with a 4:2:2:2 mixture of toluene/cyclohexane/diethyl ether/dichloromethane as eluant, affording the product in the form of a yellow oil.

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. washThe combined extracts are washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe oily residue is purified by column chromatography over silica gel with a 4:2:2:2 mixture of toluene/cyclohexane/diethyl ether/dichloromethane as eluant
  7. customaffording the product in the form of a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-3ca6835f18eb423db1c78c83a7b9bce0
Quelldatensatz
uspto-grants-1985_02
Patentnummer
US04497647

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