Malic Acid → HCID 20092141, Verbindung

HRID 274185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 274185
C([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23](O)[CH2:24][CH2:25][O:26][CH2:27][CH2:28][CH3:29])=[C:17]([F:31])[N:16]=1)CCCCCCC.O1C(CCOCCC)C1.C(O)(=O)C(CC(O)=O)O.[CH2:50]([O:58]C1C=CC(C2C=CC(O)=C(F)N=2)=CC=1)[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57].CCN(S(F)(F)[F:79])CC>C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C.C(Cl)Cl>[CH2:50]([O:58][C:13]1[CH:14]=[CH:9][C:10]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]([F:79])[CH2:24][CH2:25][O:26][CH2:27][CH2:28][CH3:29])=[C:17]([F:31])[N:16]=2)=[CH:11][CH:12]=1)[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57]

Komponenten

9

Edukt 5

HCID 525Malic AcidHCID 123472(Diethylamino)sulfur trifluorideHCID 190469612-(4-Octyloxyphenyl)-5-hydroxy-6-fluoropyridineHCID 20087472HCID 20087472, VerbindungHCID 20092120HCID 20092120, Verbindung

Produkt 1

HCID 20092141HCID 20092141, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 6569Methyl Ethyl KetoneLösungsmittelHCID 11430Potassium CarbonateLösungsmittel

Versuchsvorschrift

A solution of 0.1 mol of 2-(octylphenyl)-5-(2-hydroxy-5-oxaoctyloxy)-6-fluoropyridine (prepared by heating optically active 1,2-epoxy-5-oxaoctane, obtainable from malic acid, with 2C in the presence of dry potassium carbonate and methyl ethyl ketone as solvent) in methylene chloride is cooled to -40° C., and 0.11 mol of DAST is added dropwise thereto with exclusion of moisture. The reaction mixture is subsequently stirred for 12 hours with slow warming to room temperature. The reaction mixture is then hydrolyzed with ice cooling and washed with dilute sodium hydroxide solution and several times with water. The mixture is dried over magnesium sulfate, the solvent is removed on a rotary evaporator, and the crude product is purified by chromatography and by crystallization, giving optically active 2-(4-octyloxyphenyl)-5-(2-fluoro-5-oxaoctyloxy)-6-fluoropyridine.

Aufarbeitung

  1. washhydrolyzed with ice cooling and washed with dilute sodium hydroxide solution and several times with water
  2. dry with materialThe mixture is dried over magnesium sulfate
  3. customthe solvent is removed on a rotary evaporator
  4. customthe crude product is purified by chromatography and by crystallization

Quellen und Nachweise

ORD-Eintrag
ord-8fd6934632eb435faa314ac7bd2c8327
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05389291

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