N,N,N',N'-Tetramethylethylenediamine → Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

HRID 129275Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 129275
CN(C)CCN(C)C.[CH3:9][O:10][C:11]([CH:13]1[CH2:18][CH2:17][CH:16]([C:19](Cl)=[O:20])[CH2:15][CH2:14]1)=[O:12]>C1COCC1.[BH4-].[Zn+2].[BH4-]>[OH:20][CH2:19][CH:16]1[CH2:15][CH2:14][CH:13]([C:11]([O:10][CH3:9])=[O:12])[CH2:18][CH2:17]1

Komponenten

5

Edukt 2

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 15380636Methyl 4-(chlorocarbonyl)cyclohexane-1-carboxylate

Produkt 1

HCID 11073869Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 12838295ZINC;boranuideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Zinc borohydride solution (67 ml of a 0.35M solution, Ref. W. J. Gensler et al J. Amer. Chem. Soc. 1960, 82, 6074) and tetramethylethylenediamine (TMEDA) were successively added to a stirred solution of 4-methoxycarbonylcyclohexylcarbonyl chloride (1.02 g) in THF (18 ml) at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes. The organic phase was then washed with dilute hydrochloric acid and brine before drying over anhydrous magnesium sulphate and then evaporation in vacuo. Methyl 4-hydroxymethylcyclohexanecarboxylate was obtained as a semi-crystalline oil.

Aufarbeitung

  1. washThe organic phase was then washed with dilute hydrochloric acid and brine
  2. dry with materialbefore drying over anhydrous magnesium sulphate
  3. customevaporation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ab524fbbb2b84d72923eee9dfce3557b
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466710

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