Potassium Hydroxide → HCID 15674626, compound

HRID 1756113Notes

Reaction equation

HRID 1756113 reaction equation
[OH-].[K+].C(O[CH:7]1[C:15]2[C:10](=[C:11]([CH3:21])[C:12]([CH2:17]COC)=[C:13]([CH3:16])[CH:14]=2)[C:9](=[O:22])[CH:8]1[CH3:23])(=O)C>O1CCCC1.[Zn]>[CH3:23][C:8]1[C:9](=[O:22])[C:10]2[C:15]([CH:7]=1)=[CH:14][C:13]([CH3:16])=[C:12]([CH3:17])[C:11]=2[CH3:21]

Participants

5

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 19419367HCID 19419367, compound

Product 1

HCID 15674626HCID 15674626, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The 2,5,6,7-tetramethyl-1-indenone was prepared by reducing 2,4,5,6-tetramethyl-1,3-indanione 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: ##STR8## 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: ##STR9## R=H Dehydropterosin B R=CH3Dehydropterosin O

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##STR8## 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-fa6f191563fa45efae0816d731946f72
Source dataset
uspto-grants-1995_08
Patent number
US05439936

Reaction notes

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