Diethyl Oxalate → HCID 11096938, compound

HRID 1434735Notes

Reaction equation

HRID 1434735 reaction equation
[CH2:1]([CH2:8][C:9](=[O:11])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12]([O:14][C:15](=[O:21])[C:16](OCC)=[O:17])[CH3:13].CC[O-].[Na+]>>[CH2:12]([O:14][C:15](=[O:21])[C:16](=[O:17])[CH2:10][C:9](=[O:11])[CH2:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:13]

Participants

4

Reactant 3

HCID 7268Diethyl OxalateHCID 17355Benzyl acetoneHCID 2723922Sodium ethoxide

Product 1

HCID 11096938HCID 11096938, compoundYield 43.9%

Procedure

Benzylacetone (1.0 g, 6.75 mmol) and diethyloxalate (0.92 mL, 6.75 mmol) were mixed together, and then added to a solution of NaOEt (˜3 M, 2.3 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 19. The crude material was purified with 1:1 Hexanes:CH2Cl2 to obtain 0.7348 g (43.9%) of 19. 1H (CD3OD, 400 MHz): δ 7.27-7.12 (5H, m), 4.26 (2H, q, J=7.2 Hz), 2.89 (2H, t, J=7.3 Hz), 2.81 (2H, t, J=7.3 Hz), 1.30 (3H, t, J=7.1 Hz) ppm. Partial 13C (CD3OD, 100 MHz): δ 163.32, 141.74, 129.43, 129.29, 127.16, 126.95, 103.06, 63.34, 43.46, 31.34, 14.24 ppm. DEPT (CD3OD, 100 MHz): CH3 carbons: 14.24; CH2 carbons: 63.34, 43.46, 31.34; CH carbons: 129.43, 129.29, 127.16, 103.06 ppm. HPLC: 10.279 min.

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 19
  10. customThe crude material was purified with 1:1 Hexanes

Sources & evidence

ORD record
ord-e4186e428c964c2084ae282492cf5b94
Source dataset
uspto-grants-2009_11
Patent number
US07615572B2

Reaction notes

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