Potassium Carbonate → Octahydropentalenol

HRID 462791Notes

Reaction equation

HRID 462791 reaction equation
[CH:1]12[CH2:8][CH2:7][CH2:6][CH:5]1[CH2:4][CH2:3][CH2:2]2.C(=O)([O-])[O-:10].[K+].[K+]>CO>[OH:10][CH:2]1[CH2:3][CH2:4][CH:5]2[CH:1]1[CH2:8][CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 136508Octahydropentalene

Product 1

HCID 549090Octahydropentalenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of (E)-6-acetoxy-2-[(mixture of 3α and 3β)-tert-butyldimethylsilyloxyoct-1-enyl]bicyclo[3,3,0]octane (530 mg; prepared as described in Reference Example 24 and predominantly in the 2β-configuration) in methanol (10 ml) was treated with anhydrous potassium carbonate (193 mg). The mixture was heated at 40° C., with stirring, for 24 hours. The methanol was then removed in vacuo and the residue was extracted with dichloromethane (3×10 ml). Concentration of the extract in vacuo gave (E)-2-[(mixture of 3α and 3β)-tert-butyldimethylsilyloxyoct-1-enyl]-6-hydroxybicyclo[3,3,0]octane (430 mg), predominantly in the 2β-configuration.

Workup

  1. customprepared
  2. customThe methanol was then removed in vacuo
  3. extractionthe residue was extracted with dichloromethane (3×10 ml)
  4. extractionConcentration of the extract in vacuo

Sources & evidence

ORD record
ord-757602d6a0494862acc314d7386b6c6f
Source dataset
uspto-grants-1985_05
Patent number
US04517202

Reaction notes

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