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Selenium Dioxide → (4alphaR,5R,6R,7S)-6,7-Dihydroxy-4alpha,5,6,7-tetrahydro-3,4alpha,5-trimethylnaphtho(2,3-b)furan-2(4H)-one

HRID 1383629
Notes
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Reaction equation

HRID 1383629 reaction equation
[OH:1][C@H:2]1[CH2:16][CH:15]=[C:14]2[C@:4]([CH3:17])([CH2:5][C:6]3[C:7](=[CH:13]2)[O:8][C:9](=[O:12])[C:10]=3[CH3:11])[C@H:3]1[CH3:18].[Se](=O)=[O:20]>O1CCOCC1>[OH:1][C@H:2]1[C@@H:16]([OH:20])[CH:15]=[C:14]2[C@:4]([CH3:17])([CH2:5][C:6]3[C:7](=[CH:13]2)[O:8][C:9](=[O:12])[C:10]=3[CH3:11])[C@H:3]1[CH3:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 10514571HCID 10514571, compound

Product 1

HCID 10084054(4alphaR,5R,6R,7S)-6,7-Dihydroxy-4alpha,5,6,7-tetrahydro-3,4alpha,5-trimethylnaphtho(2,3-b)furan-2(4H)-oneYield 86%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

The compound prepared in Example B1 (5 mg, 0.02 mmol) was dissolved in dioxane (1 ml), selenium dioxide (22 mg, 0.20 mmol) was added thereto, and the mixture was stirred at 50° C. for 2 days. The reaction solution was filtered, and the solvent was removed by distillation under reduced pressure. The residue was purified by preparative TLC (hexane:ethyl acetate=1:1) to give the title compound (4.5 mg, 86%).

Workup

  1. filtrationThe reaction solution was filtered
  2. customthe solvent was removed by distillation under reduced pressure
  3. customThe residue was purified by preparative TLC (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-519a06bf78c04e78b8b20d3b0ee282a9
Source dataset
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06255339B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes