Diethyl Oxalate → HCID 15751935, compound

HRID 1724728Notes

Reaction equation

HRID 1724728 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][C:3]1=[O:7].C(O[C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])C.CC[O-].[Na+]>>[CH2:15]([O:14][C:12](=[O:13])[C:11]([CH:4]1[CH2:5][CH2:6][CH:2]([CH3:1])[C:3]1=[O:7])=[O:17])[CH3:16]

Participants

4

Reactant 3

HCID 7268Diethyl OxalateHCID 142652-MethylcyclopentanoneHCID 2723922Sodium ethoxide

Product 1

HCID 15751935HCID 15751935, compoundYield 27.9%

Procedure

2-methylcyclopentanone (1.0058 g, 10.2 mmol) and diethyloxalate (1.38 mL, 10.2 mmol) were mixed together, and then added to a solution of NaOEt (˜3 M, 3.4 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 4. The crude material was purified with 98:2 to 96:4 Hexanes: EtOAc to obtain 0.5635 g (27.7%) of 4. 1H (CDCl3, 400 MHz): δ 4.29 (2H, q, J=7.1 Hz), 2.96 (1H, ddd, J=17.6, 8.1, 1.5 Hz), 2.69 (1H, ddd, J=17.6, 9.5, 8.1 Hz), 2.57-2.47 (1H, m), 2.24 (1H, dtd, J=12.5, 8.3, 2.4 Hz), 1.49 (1H, dtd, J=12.5, 10.3, 8.4 Hz), 1.34 (3H, t, J=7.1 Hz), 1.13 (3H, d, J=7.0 Hz) ppm. 13C (CDCl3, 100 MHz): δ 164.09, 153.19, 117.67, 62.92, 44.76, 30.60, 30.36, 26.55, 14.63, 14.37 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 4
  10. customThe crude material was purified with 98:2 to 96:4 Hexanes

Sources & evidence

ORD record
ord-64e6394b707f45338a1e335494c2f3e0
Source dataset
uspto-grants-2009_02
Patent number
US07488747B2

Reaction notes

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