Sodium Bicarbonate → 6-Acetoxy-2-formylbicyclo[3,3,0]octane

HRID 462789Notes

Reaction equation

HRID 462789 reaction equation
[C:1]([O:4][CH:5]1[CH2:12][CH2:11][CH:10]2[CH:6]1[CH2:7][CH2:8][CH:9]2[CH2:13][OH:14])(=[O:3])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([O:4][CH:5]1[CH2:12][CH2:11][CH:10]2[CH:6]1[CH2:7][CH2:8][CH:9]2[CH:13]=[O:14])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 203972176-Acetoxy-2-hydroxymethylbicyclo[3,3,0]octaneHCID 178418287HCID 178418287, compound

Product 1

HCID 203971916-Acetoxy-2-formylbicyclo[3,3,0]octane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 6-acetoxy-2-hydroxymethylbicyclo[3,3,0]octane (0.10 g; prepared as described in Reference Example 20 and predominantly in the 2β-configuration) in dry dichloromethane (2.5 ml) was treated with pyridinium chlorochromate (0.22 g) and anhydrous sodium bicarbonate (0.083 g). The resulting suspension was stirred for 150 minutes at the ambient temperature and was then placed directly onto a short column of silica gel and subjected to medium pressure, short column chromatography, eluting with a mixture of ethyl acetate and toluene (1:1 v/v) to give 6-acetoxy-2-formylbicyclo[3,3,0]octane (0.070 g), predominantly in the 2β-configuration.

Workup

  1. customprepared
  2. washeluting with a mixture of ethyl acetate and toluene (1:1 v/v)

Sources & evidence

ORD record
ord-2b5115520080487b99b24e50dd863a8a
Source dataset
uspto-grants-1985_05
Patent number
US04517202

Reaction notes

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