Diethyl Succinate → HCID 22134796, compound

HRID 908057Notes

Reaction equation

HRID 908057 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=O.CC(C)([O-:25])C.[K+].C([O-])(=O)C.[Na+]>C1COCC1.CC(O)(C)C.C(OC(=O)C)(=O)C.CCOC(C)=O.CCCCCC>[C:16]([O:15][C:13]1[C:8]2[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:9]=2)[CH:6]=[C:11]([C:10]([O:19][CH2:20][CH3:21])=[O:18])[CH:12]=1)(=[O:25])[CH3:17]

Participants

9

Reactant 4

HCID 31249Diethyl SuccinateHCID 707414-BromobenzaldehydeHCID 517045Sodium AcetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 22134796HCID 22134796, compoundYield 11%

Reagents, catalysts & solvents 4

HCID 6386tert-ButanolSolventHCID 7918Acetic AnhydrideSolventHCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 24.60 g (132.9 mmol) of 4-bromobenzaldehyde 30.66 g (176.0 mmol) of diethyl succinate in 20 ml of THF was added 200.0 ml of potassium tert-butoxide in 1.0 M 2-methyl-2-propanol over a period of 20 minutes. The reaction mixture was reflux overnight, then cooled to room temperature. The mixture was extracted with EtOAc, washed with 10% HCl, brine, and water, dried (MgSO4), filtered, and concentrated to afford a yellow-brown oil. The mixture in 150.0 ml of acetic anhydride was added 10.0 g of sodium acetate and was reflux overnight, then cooled to room temperature. The mixture was extracted with EtOAc, washed with 10% HCl, brine, and water, dried (MgSO4), filtered, and concentrated. Flash column chromatography (20% EtOAc/hexane) yielded a brown oil. (5.10 g, 11% yield): Rf0.22 (10% EtOAc/hexane); 1H NMR (400 MHz, CDCl3) δ 1.43 (t, J=7.2 Hz, 3, CH3), 2.60 (s, 3, CH3), 4.42 (q, J=7.2 Hz, 2, CH2), 7.40 (d, J=2.4 Hz, 1, ArH), 7.65 (dd, J=7.6, 2.4 Hz, 1, ArH), 7.84 (d, J=8.0 Hz, 1, ArH), 8.05 (s, 1, ArH), 8.46 ppm (s, 1, ArH).

Workup

  1. temperatureThe reaction mixture was reflux overnight
  2. extractionThe mixture was extracted with EtOAc
  3. washwashed with 10% HCl, brine, and water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford a yellow-brown oil
  8. temperaturewas reflux overnight
  9. temperaturecooled to room temperature
  10. extractionThe mixture was extracted with EtOAc
  11. washwashed with 10% HCl, brine, and water
  12. dry with materialdried (MgSO4)
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customFlash column chromatography (20% EtOAc/hexane) yielded a brown oil

Sources & evidence

ORD record
ord-9251899382cc408a99a8c98f08687b0b
Source dataset
uspto-grants-2011_09
Patent number
USRE042700E1

Reaction notes

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