2-Propanone, dimethylhydrazone → 4-Hydroxy-5-[4-(4-trifluoromethylphenoxy)phenoxy]-2-hexanone N,N-dimethylhydrazone

HRID 2417650Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2417650
[CH3:1][N:2]([CH3:7])[N:3]=[C:4]([CH3:6])[CH3:5].C([N-]C(C)C)(C)C.[Li+].[F:16][C:17]([F:37])([F:36])[C:18]1[CH:35]=[CH:34][C:21]([O:22][C:23]2[CH:33]=[CH:32][C:26]([O:27][CH:28]([CH3:31])[CH:29]=[O:30])=[CH:25][CH:24]=2)=[CH:20][CH:19]=1.O.C(Cl)Cl>O1CCCC1>[CH3:1][N:2]([CH3:7])[N:3]=[C:4]([CH2:6][CH:29]([OH:30])[CH:28]([O:27][C:26]1[CH:25]=[CH:24][C:23]([O:22][C:21]2[CH:34]=[CH:35][C:18]([C:17]([F:37])([F:16])[F:36])=[CH:19][CH:20]=2)=[CH:33][CH:32]=1)[CH3:31])[CH3:5]

Komponenten

6

Edukt 4

HCID 1394772-Propanone, dimethylhydrazoneHCID 2724682Lithium diisopropylamideHCID 128567812-[4-(4-Trifluoromethylphenoxy)phenoxy]propanalHCID 21908982Water methylene chloride

Produkt 1

HCID 544292334-Hydroxy-5-[4-(4-trifluoromethylphenoxy)phenoxy]-2-hexanone N,N-dimethylhydrazone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of acetone N,N-dimethylhydrazone (6.5 mmol) in tetrahydrofuran (THF; 15 ml) under nitrogen is added lithium diisopropylamide (LDA; 7.2 mmol) in THF (15 ml) at 0° for 5 hours. The resulting solution is cooled to -78°, and to it is added 2-[4-(4-trifluoromethylphenoxy)phenoxy]propanal (7.2 mmol). After 1 hour at -78°, the reaction mixture is allowed to warm to 0° and is poured into water/methylene chloride (3:1). The organic phase is separated (3X), and the combined organic extracts are dried over sodium sulfate and concentrated to give 4-hydroxy-5-[4-(4-trifluoromethylphenoxy)-phenoxy]-2-hexanone N,N-dimethylhydrazone (cpd. 1, Table A).

Aufarbeitung

  1. temperatureThe resulting solution is cooled to -78°
  2. temperatureto warm to 0°
  3. customThe organic phase is separated (3X)
  4. dry with materialthe combined organic extracts are dried over sodium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6817bbfd7bb74d468c718bcfc7a84da3
Quelldatensatz
uspto-grants-1984_09
Patentnummer
US04469872

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