Ammonium Chloride → Ethyl 4,5-dichloro-6-((1-ethoxymethyl-pyrazol-5-yl)-hydroxymethyl)-1,3-benzodioxole-2-carboxylate

HRID 1074177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1074177
C([Li])CCC.[CH2:6]([O:8][CH2:9][N:10]1[CH:14]=[CH:13][CH:12]=[N:11]1)[CH3:7].[Cl:15][C:16]1[C:24]2[O:23][CH:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[O:21][C:20]=2[CH:19]=[C:18]([CH:30]=[O:31])[C:17]=1[Cl:32].[Cl-].[NH4+]>CCCCCC.O1CCCC1.CN(C)P(=O)(N(C)C)N(C)C>[Cl:15][C:16]1[C:24]2[O:23][CH:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[O:21][C:20]=2[CH:19]=[C:18]([CH:30]([C:14]2[N:10]([CH2:9][O:8][CH2:6][CH3:7])[N:11]=[CH:12][CH:13]=2)[OH:31])[C:17]=1[Cl:32]

Komponenten

8

Edukt 4

HCID 25517Ammonium ChlorideHCID 14748638Ethyl 4,5-dichloro-6-formyl-1,3-benzodioxole-2-carboxylateHCID 157143991-(ethoxymethyl)-1H-pyrazoleHCID 178418339Butyllithium

Produkt 1

HCID 15052557Ethyl 4,5-dichloro-6-((1-ethoxymethyl-pyrazol-5-yl)-hydroxymethyl)-1,3-benzodioxole-2-carboxylateAusbeute 28,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittelHCID 12679HexamethylphosphoramideLösungsmittel

Versuchsvorschrift

1.25 ml of 1.6M n-butyl lithium in n-hexane is added dropwise to a solution of 252 mg of 1-ethoxymethyl-pyrazole in 5 ml of tetrahydrofuran at -60° to -50° C. 0.4 ml of hexamethylphosphoric triamide is added to the mixture and the mixture is stirred at the same temperature for 1 hour. The mixture is added to a solution of 582 mg of ethyl 4,5-dichloro-6-formyl-1,3-benzodioxole-2-carboxylate in 10 ml of tetrahydrofuran at -60° to -50° C. and the mixture is stirred at the same temperature for 5 minutes. An aqueous saturated ammonium chloride solution is added to the mixture and the mixture is extracted with ethyl acetate. The extract is washed, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography (solvent; chloroform-acetone-ethanol) to give 240 mg of ethyl 4,5-dichloro-6-[(1-ethoxymethyl-pyrazol-5-yl)-hydroxymethyl]-1,3-benzodioxole-2-carboxylate.

Aufarbeitung

  1. stirringthe mixture is stirred at the same temperature for 5 minutes
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe extract is washed
  4. customdried
  5. customevaporated
  6. customto remove solvent
  7. customThe residue is purified by silica gel column chromatography (solvent; chloroform-acetone-ethanol)

Quellen und Nachweise

ORD-Eintrag
ord-be189844d4874b7389c21d38bfbe251d
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04973600

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