4-Formyl-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester → Bicyclo[3.2.1]octane-1,4-dicarboxylic acid 1-ethyl ester

HRID 480121Notes

Reaction equation

HRID 480121 reaction equation
[CH2:1]([O:3][C:4]([C:6]12[CH2:13][CH:10]([CH2:11][CH2:12]1)[CH:9]([CH:14]=[O:15])[CH2:8][CH2:7]2)=[O:5])[CH3:2].CC(C)=[O:18].OS(O)(=O)=O.O=[Cr](=O)=O>>[CH2:1]([O:3][C:4]([C:6]12[CH2:13][CH:10]([CH2:11][CH2:12]1)[CH:9]([C:14]([OH:18])=[O:15])[CH2:8][CH2:7]2)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 872605574-Formyl-bicyclo[3.2.1]octane-1-carboxylic acid ethyl esterHCID 131709961Jones' reagent

Product 1

HCID 67079138Bicyclo[3.2.1]octane-1,4-dicarboxylic acid 1-ethyl esterYield 87%

Procedure

To an ice-cold solution of 4-formyl-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester (3.85 mmol, 0.81 g) was added slowly Jones reagent (2.7 M, 1.43 mL). The reaction was stirred at ice temperature 20 min, then quenched by addition of iPrOH. diluted with H2O and extracted with Et2O (3×). The combined organic extracts were washed with H2O (2×), brine (1×), and dried (MgSO4). Filtration and evaporation provided the viscous oily bicyclo[3.2.1]octane-1,4-dicarboxylic acid 1-ethyl ester (0.76 g, 87%) as a mixture of axial and equatorial acids. 13C NMR (100 MHz, CDCl3): 14.16 (q), 19.86 (t), 21.07 (t), 25.98 (t), 29.20 (t), 31.52 (t), 31.87 (t), 32.27 (t), 33.39 (t), 37.80 (d), 38.07 (t), 38.10 (d), 42.06 (t), 44.80 (d), 45.78 (d), 49.38 (s), 49.60 (s), 60.31 (t), 60.36 (t), 177.08 (s), 180.01 (s).

Workup

  1. customquenched by addition of iPrOH
  2. additiondiluted with H2O
  3. extractionextracted with Et2O (3×)
  4. washThe combined organic extracts were washed with H2O (2×), brine (1×)
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-0485b0ddb78e4828ad054b78c87e8da7
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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