Triethylamine → 7-(2-Quinolinylmethoxy)heptan-1-ol

HRID 1196562Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1196562
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[Na].Cl.Cl[CH2:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[N:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][C:14]=1[CH2:13][O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:9]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 123811,7-HeptanediolHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 5360545Sodium

Produkt 1

HCID 198986807-(2-Quinolinylmethoxy)heptan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

1,7-Heptanediol (ex Lancaster) (1.7 g) was reacted with sodium (0.24 g) in toluene (50 ml) as in Stage A(ii). 2-Chloromethylquinoline hydrochloride (ex Aldrich) was added followed by triethylamine (0.7 ml). After heating under reflux for 6 hours, the reaction mixture was partitioned between water and diethyl ether and the organic phase washed with brine and dried. The crude material was purified by chromatography on silica (eluting with ether-hexane) to give 7-(2-quinolinylmethoxy)heptan-1-ol (0.43 g) which was used in Stage b.

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureunder reflux for 6 hours
  3. customthe reaction mixture was partitioned between water and diethyl ether
  4. washthe organic phase washed with brine
  5. customdried
  6. customThe crude material was purified by chromatography on silica (eluting with ether-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-18a6a55b3384402b8389ceca493e72ce
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05114940

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