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1,10-Phenanthroline → ethyl 4-((1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yloxy)benzoate

HRID 1798443
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1798443
I[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH3:13][C@H:14]1[C@H:19]([OH:20])[CH2:18][C@@H:17]2[CH2:21][C@H:15]1[C:16]2([CH3:23])[CH3:22].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu](I)I>[CH3:13][C@H:14]1[C@H:19]([O:20][C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:18][C@@H:17]2[CH2:21][C@H:15]1[C:16]2([CH3:22])[CH3:23]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 142891Ethyl 4-iodobenzoateHCID 10524983(-)-Isopinocampheol

Produkt 1

HCID 67388677ethyl 4-((1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yloxy)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717
Copper iodide
Katalysator
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Ethyl 4-iodobenzoate (276 mg), (1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol (154 mg), 1,10-phenanthroline (36 mg), copper iodide (19 mg) and cesium carbonate (652 mg) were combined in toluene (0.5 mL). The reaction was heated to 120° C. over 36 hours. The reaction mixture was removed from heat, allowed to cool, diluted with ethyl acetate and poured into water. The organic layer was washed thoroughly with water and brine, dried over MgSO4, filtered and concentrated under vacuum. The crude material was purified by flash chromatography eluting with 95/5 hexanes/ether.

Aufarbeitung

  1. customThe reaction mixture was removed
  2. temperaturefrom heat
  3. temperatureto cool
  4. additiondiluted with ethyl acetate
  5. additionpoured into water
  6. washThe organic layer was washed thoroughly with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe crude material was purified by flash chromatography
  11. washeluting with 95/5 hexanes/ether

Quellen und Nachweise

ORD-Eintrag
ord-128c9fe2385b4fe09aab780e8c377f6d
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08343967B2

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