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Water → 2-(3-(1-Hydroxyhexyl)benzyloxymethyl)quinoline

HRID 414845
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 414845
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.C1(C)C=CC(S(O[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([OH:36])[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:25]=2)(=O)=O)=CC=1.C(N(CC)CC)C.O>C(Cl)Cl>[OH:36][CH:30]([C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[CH2:23][O:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 731962-QuinolinemethanolHCID 14349156HCID 14349156, Verbindung

Produkt 1

HCID 143491382-(3-(1-Hydroxyhexyl)benzyloxymethyl)quinolineAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 2-hydroxymethylquinoline (8 g, 0.05 mol) and 3-(1-hydroxyhexyl)benzyl p-toluenesulfonate (18.2 g, 0.05 mol; prepared as in Example 17) in methylene chloride (200 ml) containing triethylamine (15 ml) was stirred at 0° C. for 4 hours, and then allowed to warm up to room temperature. This mixture was stirred for two more hours at this temperature, and then poured into water. The organic layer was separated and washed with dilute sodium hydroxide solution, water and brine. After drying the organics, all volatiles were removed to obtain the crude product as a yellowish brown liquid. This was purified by chromatography on silica gel using 15% ethyl acetate in hexanes to get the pure product as a clear, light yellow liquid (9 g, 52% yield).

Aufarbeitung

  1. temperatureto warm up to room temperature
  2. stirringThis mixture was stirred for two more hours at this temperature
  3. customThe organic layer was separated
  4. washwashed with dilute sodium hydroxide solution, water and brine
  5. customAfter drying the organics, all volatiles
  6. customwere removed
  7. customto obtain the crude product as a yellowish brown liquid
  8. customThis was purified by chromatography on silica gel using 15% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-dc306c2b8cba4440b81679cf03bb421f
Quelldatensatz
uspto-grants-1988_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04794188

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