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 1879344Notes

Reaction equation

HRID 1879344 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 126575751,4,4a,5,8,8a-Hexahydro-1,4-ethanonaphthalene-5,8-diolYield 106.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f94c1a785c364590b5151d146b8595fd
Source dataset
uspto-grants-2012_11
Patent number
US08314253B2

Reaction notes

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