Diethyl Oxalate → HCID 57435070, compound

HRID 1366871Notes

Reaction equation

HRID 1366871 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:10])[CH2:8][CH2:7][CH2:6][C:5]1=[O:9].[CH2:11]([O:13][C:14](=[O:20])[C:15](OCC)=[O:16])[CH3:12].CC[O-].[Na+]>CCO>[CH2:11]([O:13][C:14](=[O:20])[C:15]([CH:6]1[CH2:7][CH2:8][C:4]([CH3:10])([CH3:3])[C:5]1=[O:9])=[O:16])[CH3:12]

Participants

6

Reactant 4

HCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 1382862,2-DimethylcyclopentanoneHCID 2723922Sodium ethoxide

Product 1

HCID 57435070HCID 57435070, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydride (0.428 g, 17.8 mmol) was added slowly to a NaCl ice bath containing EtOH (5.4 mL, 3.3 M) stirring under N2. 2,2-dimethylcyclopentanone (2.00 g, 17.83 mmol) and diethyloxalate (2.42 mL, 17.8 mmol) were mixed together, and then added to the chilled NaOEt solution. After stirring for 15 minutes, the reaction was warmed to room temperature and stirred for 6 hours, at which point the reaction was judged complete by TLC. 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 3.4084 g (90.0%) of crude 2 that was sufficiently pure by NMR to go on to the next step without further purification. Note: NaOEt purchased from Aldrich may be substituted for the NaOEt synthesized in situ. 1H (CDCl3, 400 MHz): δ 4.29 (2H, q, J=7.3 Hz), 2.82 (2H, t, J=7.3 Hz), 1.76 (2H, t, J=7.3 Hz), 1.32 (3H, t, J=7.3 Hz), 1.07 (6H, s) ppm. 13C (CDCl3, 100 MHz): δ 218, 162.89, 153.15, 115.98, 62.12, 46.16, 36.39, 23.98, 23.87, 14.22 ppm.

Workup

  1. stirringAfter stirring for 15 minutes
  2. stirringstirred for 6 hours, at which
  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 3.4084 g (90.0%) of crude 2 that
  10. customto go on to the next step without further purification
  11. customsynthesized in situ

Sources & evidence

ORD record
ord-214917e20df24753afc98b643f5bbbc4
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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