Potassium Hydroxide → HCID 20131160, Verbindung

HRID 1380113Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1380113
[OH:1][CH:2]([CH2:9][O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.[OH-].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH:31]([CH3:33])[CH3:32])=[O:29].[Cl-].[NH4+]>CS(C)=O>[N:4]1([CH2:3][CH:2]([CH2:9][O:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[O:1][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH:31]([CH3:32])[CH3:33])=[O:29])[CH:8]=[CH:7][N:6]=[CH:5]1

Komponenten

6

Edukt 4

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 549816Isopropyl 6-bromohexanoateHCID 13590265HCID 13590265, Verbindung

Produkt 1

HCID 20131160HCID 20131160, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

1-[2-Hydroxy-3-[(4-methoxyphenyl)methoxy]propyl]-1H-imidazole (Example 1b; 10 g, 0.038 mol) was added to a stirred suspension of powdered potassium hydroxide (8 g, 0.14 mol) in dimethylsulphoxide (20 ml) at 18° C. and stirred for 0.5 hours. Isopropyl 6-bromohexanoate (10.5 g, 0.044 mol) was then added and the mixture was stirred for 0.5 hours at 18° C. The mixture was poured into saturated aqueous ammonium chloride (1500 ml) and extracted with dichloromethane. The combined extracts were dried (Na2SO4) and the solvent was evaporated off under reduced pressure to give the crude product which was purified by column chromatography (silica gel, 2% ethanol in chloroform) to give isopropyl 6-[2-(1H-imidazol-1-yl)-1-[[(4-methoxyphenyl)methoxy]methyl]ethoxy]hexanoate as a pale-yellow oil.

Aufarbeitung

  1. stirringthe mixture was stirred for 0.5 hours at 18° C
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. customthe solvent was evaporated off under reduced pressure
  5. customto give the crude product which
  6. customwas purified by column chromatography (silica gel, 2% ethanol in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-b73c89241d3841f9b687a95d2adf7234
Quelldatensatz
uspto-grants-1986_04
Patentnummer
US04579862

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