Endo-1,4a,8,8a-tetrahydro-1,4-ethanonaphthalene-5,8-dione → 1,4,4a,5,8,8a-Hexahydro-1,4-ethanonaphthalene-5,8-diol

HRID 1879344

Reaktionsgleichung

Reaktionsgleichung von HRID 1879344
[CH:1]12[CH2:12][CH2:11][CH:8]([CH:9]=[CH:10]1)[CH:7]1[CH:2]2[C:3](=[O:14])[CH:4]=[CH:5][C:6]1=[O:13].[BH4-].[Na+]>CO>[CH:8]12[CH2:11][CH2:12][CH:1]([CH:10]=[CH:9]1)[CH:2]1[CH:7]2[CH:6]([OH:13])[CH:5]=[CH:4][CH:3]1[OH:14]

Komponenten

4

Edukt 2

HCID 137731Endo-1,4a,8,8a-tetrahydro-1,4-ethanonaphthalene-5,8-dioneHCID 4311764Sodium borohydride

Produkt 1

HCID 126575751,4,4a,5,8,8a-Hexahydro-1,4-ethanonaphthalene-5,8-diolAusbeute 106,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 25.6 g of tricyclo[6.2.2.02,7]dodeca-4,9-diene-3,6-dione in 600 mL of MeOH were added 58.0 g of CeCl3 7H2O. Then, 5.7 g of NaBH4 were portionwise added at 0° C. and the mixture was stirred for 1 h at the same temperature. After evaporation of the solvent the residue was redissolved in EtOAc, it was washed with H2O, dried over MgSO4 and concentrated in vacuo. The crude was again redissolved in EtOAc and triturated with Hept to obtain 27.9 g of the desired compound as mixture of stereoisomers as brownish solid.

Aufarbeitung

  1. customAfter evaporation of the solvent the residue
  2. dissolutionwas redissolved in EtOAc
  3. washit was washed with H2O
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude was again redissolved in EtOAc
  7. customtriturated with Hept

Quellen und Nachweise

ORD-Eintrag
ord-f94c1a785c364590b5151d146b8595fd
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08314253B2

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