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Acetic Acid → Diisopropyl Ether

HRID 2243345
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2243345
[F:1][C:2]1[C:25]([F:26])=[CH:24][C:5]2[NH:6][C:7]([C:9]3[C:21]4[C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14](=[N:22]O)[C:13]=4[CH:12]=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1.[C:27]([OH:30])(=O)[CH3:28].[CH2:31](O)C>O.[Zn]>[CH:27]([O:30][CH:25]([CH3:24])[CH3:2])([CH3:28])[CH3:31].[F:26][C:25]1[C:2]([F:1])=[CH:3][C:4]2[NH:8][C:7]([C:9]3[C:21]4[C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[CH:14]([NH2:22])[C:13]=4[CH:12]=[CH:11][CH:10]=3)=[N:6][C:5]=2[CH:24]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 176Acetic AcidHCID 702EthanolHCID 137227840HCID 137227840, Verbindung

Produkt 2

HCID 7914Diisopropyl EtherHCID 67358643HCID 67358643, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysator
HCID 962
Water
Lösungsmittel

Versuchsvorschrift

The procedure used in Example 216 is followed. In a 100 ml round-bottomed flask under an argon atmosphere, dissolve 830 mg of 4-(5,6-difluoro-1H-benzimidazol-2-yl)-9H-fluoren-9-one oxime (Z,E), obtained in the previous stage, in a mixture of 5.5 ml of ethanol and 5.5 ml of water and 5.5 ml of acetic acid, at room temperature, add 624 mg of zinc in three stages, and, between each addition, stir for approximately one hour to two hours. Add Celite and filter. The filtrate is concentrated under pressure. The crude product is purified by flash chromatography on silica gel (40-63 μm), eluting with a mixture of dichloromethane and ammonia as a 7N solution in methanol (98/2 by volume). After formation of a paste with diisopropyl ether, in this way we obtain 653 mg of 4-(5,6-difluoro-1H-benzimidazol-2-yl)-9H-fluorene-9(R,S)-amine, in the form of a white powder, which is used as it is in the following stage, with the following characteristics:

Aufarbeitung

  1. additionbetween each addition
  2. filtrationAdd Celite and filter
  3. concentrationThe filtrate is concentrated under pressure
  4. customThe crude product is purified by flash chromatography on silica gel (40-63 μm)
  5. washeluting with a mixture of dichloromethane and ammonia as a 7N solution in methanol (98/2 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-71711611570a446f9308e668d285605e
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07674795B2

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