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 2105652Notes

Reaction equation

HRID 2105652 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. 13CNMR (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), 180.0.1 (s).

Workup

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

Sources & evidence

ORD record
ord-3882457c20ab432d8d609e8cd085eb7c
Source dataset
uspto-grants-2009_08
Patent number
US07579354B2

Reaction notes

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