Acetic Acid → 4-hydroxy-5-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]-2-hexanone N,N-dimethylhydrazone

HRID 1248093Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1248093
[CH3:1][N:2]([CH3:7])[N:3]=[C:4]([CH3:6])[CH3:5].[Li+].CCC[CH2-].[Cl:13][C:14]1[C:15]([O:24][C:25]2[CH:35]=[CH:34][C:28]([O:29][CH:30]([CH3:33])[CH:31]=[O:32])=[CH:27][CH:26]=2)=[N:16][CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1.C(O)(=O)C>C1COCC1>[CH3:1][N:2]([CH3:7])[N:3]=[C:4]([CH2:6][CH:31]([OH:32])[CH:30]([O:29][C:28]1[CH:27]=[CH:26][C:25]([O:24][C:15]2[C:14]([Cl:13])=[CH:19][C:18]([C:20]([F:21])([F:22])[F:23])=[CH:17][N:16]=2)=[CH:35][CH:34]=1)[CH3:33])[CH3:5]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 61028n-Butyl lithiumHCID 1394772-Propanone, dimethylhydrazoneHCID 189627072-[4-(3-Chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]propanal

Produkt 1

HCID 736742964-hydroxy-5-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]-2-hexanone N,N-dimethylhydrazone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of acetone N,N-dimethylhydrazone (0.48 g, 4.8 mmol) in 5 ml of THF is added N-butyllithium (4.8 mmol) at -65°, and the mixture is stirred for about 30 minutes. 2-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]propanal (1.50 g, 4.8 mmol) in 5 ml of THF is added dropwise. After several hours at -65°, the reaction mixture is allowed to warm to 0° and is poured onto ice made slightly acidic with 10% acetic acid. The organic phase is separated, washed with water and with NaCl and dried. Solvent is removed to give 4-hydroxy-5-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]-2-hexanone N,N-dimethylhydrazone.

Aufarbeitung

  1. waitAfter several hours at -65°
  2. temperatureto warm to 0°
  3. additionis poured onto ice
  4. customThe organic phase is separated
  5. washwashed with water and with NaCl
  6. customdried
  7. customSolvent is removed

Quellen und Nachweise

ORD-Eintrag
ord-ae86af0799fc4af4ad31be4bff83c8c9
Quelldatensatz
uspto-grants-1985_06
Patentnummer
US04522647

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