Diethyl Oxalate → Ethyl oxo(2-oxocycloheptyl)acetate

HRID 1366877Notes

Reaction equation

HRID 1366877 reaction equation
[C:1]1(=[O:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:9]([O:11][C:12](=[O:18])[C:13](OCC)=[O:14])[CH3:10].CC[O-].[Na+]>>[CH2:9]([O:11][C:12](=[O:18])[C:13](=[O:14])[CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:1]1=[O:8])[CH3:10]

Participants

4

Reactant 3

HCID 7268Diethyl OxalateHCID 10400CycloheptanoneHCID 2723922Sodium ethoxide

Product 1

HCID 13245015Ethyl oxo(2-oxocycloheptyl)acetateYield 52.3%

Procedure

Cycloheptanone (1.9998 g, 17.8 mmol) and diethyloxalate (2.42 mL, 17.8 mmol) were mixed together, and then added to a solution of NaOEt (˜3 M, 5.94 mL) stirring in an ice bath under N2. After stirring for 15 minutes, the reaction was warmed to room temperature and stirred overnight. The reaction was quenched at 0° C. with 1N HCl and extracted 2× with CH2Cl2. The combined organics were washed with H2O, dried with Na2SO4, filtered, and concentrated to yield crude 13. The crude material was purified with 1:1 Hexanes:CH2Cl2 to obtain 1.9775 g (52.3%) of 13. Note: The product was still not completely pure at this point, but was carried on to the next step. 1H (CDCl3, 400 MHz): δ 4.31 (2H, q, J=7.3 Hz), 2.66-2.58 (2H, m), 2.48-2.43 (2H, m), 1.77-1.59 (6H, m), 1.34 (3H, t, J=7.3H) ppm.

Workup

  1. stirringAfter stirring for 15 minutes
  2. stirringstirred overnight
  3. customThe reaction was quenched at 0° C. with 1N HCl
  4. extractionextracted 2× with CH2Cl2
  5. washThe combined organics were washed with H2O
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield crude 13
  10. customThe crude material was purified with 1:1 Hexanes

Sources & evidence

ORD record
ord-960d352f4f25498dabe777ad059c4715
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

Loading…