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Water → HCID 53648298, Verbindung

HRID 979174
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 979174
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[C@@H:7]([CH:12]([CH3:14])[CH3:13])[C@H:6]([OH:15])[CH2:5]2.[H-].[Na+].Br[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:21]=1.O>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[C@@H:7]([CH:12]([CH3:13])[CH3:14])[C@H:6]([O:15][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[N:21]=1)[CH2:5]2
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Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 129263872-(Bromomethyl)-6-phenoxypyridineHCID 54053742HCID 54053742, Verbindung

Produkt 1

HCID 53648298HCID 53648298, VerbindungAusbeute 83,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553
Tetrabutylammonium Iodide
Katalysator
HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

A solution of trans-5,6-dichloro-1-isopropyl-2-indanol (0.73 g), in anhydrous tetrahydrofuran (7 ml) was added to a suspension of sodium hydride (0.24 g, oil free) in anhydrous tetrahydrofuran (10 ml). The mixture was stirred for 40 minutes and a solution of 2-(bromomethyl)-6-phenoxypyridine (0.84 g) in anhydrous tetrahydrofuran was added, followed by a catalyst amount of tetra-n-butylammonium iodide, The mixture was stirred at room temperature for 18 hours, mixed with water (100 ml) and extracted with diethyl ether (3×50 ml). The combined ether extracts were dried (MgSO4) and condensed under reduced pressure to give an oil which was purified by flash chromatography to give trans-5,6-dichloro-1-isopropyl-2-((6-phenoxypyridin-2-yl)-methoxy)-indane (1.07 g).

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. extractionextracted with diethyl ether (3×50 ml)
  3. dry with materialThe combined ether extracts were dried
  4. custom(MgSO4) and condensed under reduced pressure
  5. customto give an oil which
  6. customwas purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-081427a108bb425d89ab052179a6e01f
Quelldatensatz
uspto-grants-1987_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04666925

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