Potassium Carbonate → Octahydropentalenol

HRID 462795Notes

Reaction equation

HRID 462795 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

Procedure

A mixture of (E)-6-acetoxy-2-[(mixture of 3α and 3β)-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-enyl]bicyclo[3,3,0]octane (0.4 g; prepared as described in Example 31 and predominantly in the 2β-configuration), potassium carbonate (0.15 g) and methanol (10 ml) was heated at 50° C. for 8 hours. The mixture was then cooled and concentrated in vacuo. The resulting residue was extracted with dichloromethane (3×5 ml). Concentration in vacuo of the combined extracts gave (E)-2-[(mixture of 3α and 3β)-tert-butyldimethylsilyloxy-3-cyclohexylprop-1-enyl]-6-hydroxybicyclo[3,3,0]octane, predominantly in the 2β-configuration, in the form of an oil (0.36 g), sufficiently pure enough in the next stage.

Workup

  1. customprepared
  2. temperatureThe mixture was then cooled
  3. concentrationconcentrated in vacuo
  4. extractionThe resulting residue was extracted with dichloromethane (3×5 ml)
  5. concentrationConcentration in vacuo of the combined extracts

Sources & evidence

ORD record
ord-612521c5b69e4735bfa884526e0bafbc
Source dataset
uspto-grants-1985_05
Patent number
US04517202

Reaction notes

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