Potassium Hydroxide → HCID 15674626, compound

HRID 864553Notes

Reaction equation

HRID 864553 reaction equation
[CH3:1][CH:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][C:6]([CH3:14])=[C:7]([CH3:13])[C:8]=2[CH3:12])[C:3]1=O.[OH-].[K+].C(OC1C2C(=C(C)C(CCOC)=C(C)C=2)C(=O)C1C)(=O)C>O1CCCC1.[Zn]>[CH3:1][C:2]1[C:10](=[O:11])[C:9]2[C:4]([CH:3]=1)=[CH:5][C:6]([CH3:14])=[C:7]([CH3:13])[C:8]=2[CH3:12]

Participants

6

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 19419366HCID 19419366, compoundHCID 19419367HCID 19419367, compound

Product 1

HCID 15674626HCID 15674626, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The 2,5,6,7-tetramethyl-l-indenone was prepared by reducing 2,4,5,6-tetramethyl-1,3-indandione with zinc dust at 50° C. Product was purified by chromatography with 1% ethyl acetate in benzene to yield two isomers. The major isomer was treated with 10% potassium hydroxide, then purified by sublimation. The compound has the structure: ##STR11## Dehydropterosin O synthesis: 3-acetoxy-6-(beta-methoxy)ethyl-2,5,7-trimethyl-1-indanone was dissolved in tetrahydrofuran and 10% potassium hydroxide and refluxed for two hours. The solution was then extracted three times with ether and the combined extracts chromatographed with 2% ethylacetate in benzene to yield the Dehydropterosin O compound. The compound has the structure: ##STR12##

Workup

  1. customat 50° C
  2. customProduct was purified by chromatography with 1% ethyl acetate in benzene
  3. customto yield two isomers
  4. custompurified by sublimation
  5. custom##STR11## Dehydropterosin O synthesis
  6. extractionThe solution was then extracted three times with ether
  7. customthe combined extracts chromatographed with 2% ethylacetate in benzene
  8. customto yield the Dehydropterosin O compound

Sources & evidence

ORD record
ord-6384a3a4afba4a409166f735ae3cc522
Source dataset
uspto-grants-1996_10
Patent number
US05563176

Reaction notes

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