p-Toluenesulfonic acid → HCID 68411694, compound

HRID 220231Notes

Reaction equation

HRID 220231 reaction equation
O[C:2]1([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH2:7][CH:6]2[CH2:8][CH2:9][CH:3]1[CH2:4][C:5]2=[O:10].CC1C=CC(S(O)(=O)=O)=CC=1>CC(C)=O.CCOC(C)=O>[CH3:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([C:2]2[CH:3]3[CH2:9][CH2:8][CH:6]([CH:7]=2)[C:5](=[O:10])[CH2:4]3)=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 68415225HCID 68415225, compound

Product 1

HCID 68411694HCID 68411694, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.03 g of crude 5-hydroxy-5-(4-methoxy-phenyl)-bicyclo[2.2.2]octan-2-one (intermediate K2A.1) was dissolved in 100 mL of acetone, 2.90 g of TsOH were added and the mixture was stirred at rt overnight. Then the reaction mixture was diluted with EtOAc, the organic phase washed with sat. aq. NaHCO3 and evaporated. The crude material was purified by CC with Hep-EtOAc (20:1) to yield 2.36 g of rac-(1R*,4R*)-5-(4-methoxy-phenyl)-bicyclo[2.2.2]oct-5-en-2-one.

Workup

  1. washthe organic phase washed with sat. aq. NaHCO3
  2. customevaporated
  3. customThe crude material was purified by CC with Hep-EtOAc (20:1)

Sources & evidence

ORD record
ord-69ff82052ee04dd887b71c2dfb7b0348
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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