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4-Bromodiphenyl Ether → HCID 22600006, Verbindung

HRID 1060985
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1060985
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:15]([C:22]1[CH:27]=[CH:26][C:25]([Mg]Br)=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1C=CC(OC2C=CC(Br)=CC=2)=CC=1.[Cl-].[NH4+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([C:25]2[CH:26]=[CH:27][C:22]([O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:23][CH:24]=2)([OH:14])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 75654-Bromodiphenyl EtherHCID 25517Ammonium ChlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178419636HCID 178419636, Verbindung

Produkt 1

HCID 22600006HCID 22600006, VerbindungAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To an 100 ml tetrahydrofuran solution of 3.5 g of N-tert-butoxycarbonyl-4-piperidone, a 35 ml of 4-phenoxyphenyl magnesium bromide prepared from 4-bromodiphenyl ether (0.6 mol/l tetrahydrofuran solution) was dropwise added under ice cooling and the resultant mixture was stirred for 1 hour. To the reaction mixture was added a 30 ml of saturated aqueous ammonium chloride solution. The product was extracted with ether. The extract was washed with saturated saline, dried, filtered, then concentrated under reduced pressure to give a residue, which was then purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give N-tert-butoxycarbonyl-4-(4-phenoxyphenyl)-4-piperidinol in an amount of 2.92 g (yield 45%).

Aufarbeitung

  1. additionwas dropwise added under ice cooling
  2. extractionThe product was extracted with ether
  3. washThe extract was washed with saturated saline
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a residue, which
  8. customwas then purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-5500bcd7baae4c94beac6f65950f71d9
Quelldatensatz
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06525199B1

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