Acetate → HCID 9855574, compound

HRID 1357443Notes

Reaction equation

HRID 1357443 reaction equation
C[CH:2]1[CH2:6][O:5][C:4](=O)[C:3]1=[O:8].[C:9]([O-])(=O)C.C(O)(=O)C.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1>C(O)C>[CH3:9][C:6]1[O:5][CH2:4][C:3](=[O:8])[C:2]=1[N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 175AcetateHCID 176Acetic AcidHCID 31268PyrrolidineHCID 54160766HCID 54160766, compound2×

Product 1

HCID 9855574HCID 9855574, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

From 4-Methyl-dihydro-furan-2,3-dione and pyrrolidium acetate in ethanol. A solution of 4-methyl-dihydro-furan-2,3-dione (100 mmol, prepared according to Fleck et al., Helv. Chim. Acta 1950, 33, 130), acetic acid (100 mmol) and pyrrolidine (100 mmol) in ethanol (225 mL) was refluxed for 2,5 h. After cooling down to room temperature, the solvent was removed in vacuo and the residue was taken up in water (200 mL). The solution was then extracted with diethyl ether (5×100 ml), the combined organic layers were dried over sodium sulphate and then freed from solvent in vacuo. The residual oil was dissolved in pentane/diethyl ether (3/2, v/v; 10 mL) and then applied onto a column (30×500 mm) filled with a slurry of aluminium oxide (basic activity III-IV, Merck, Darmstadt, Germany) in pentane. Chromatography was performed using pentane (300 mL; fraction A), pentane/diethyl ether (9/1, v/v; 400 mL; fraction B), pentane/diethyl ether (80/20, v/v; 400 mL; fraction C), pentane/diethyl ether (70/30, v/v; 400 mL; fraction D), pentane/diethyl ether (60/40, v/v; 400 mL; fraction E), pentane/diethyl ether (50/50, v/v; 400 mL; fraction F). Fraction F containing 2(5H)-MPF (2.25 g, 14% in yield) was collected and freed from solvent under vacuo affording the target compound as a colorless oil.

Workup

  1. customthe solvent was removed in vacuo
  2. extractionThe solution was then extracted with diethyl ether (5×100 ml)
  3. dry with materialthe combined organic layers were dried over sodium sulphate
  4. dissolutionThe residual oil was dissolved in pentane/diethyl ether (3/2, v/v; 10 mL)
  5. additionfilled with a slurry of aluminium oxide (basic activity III-IV, Merck, Darmstadt, Germany) in pentane
  6. additionFraction F containing 2(5H)-MPF
  7. custom(2.25 g, 14% in yield)
  8. customwas collected

Sources & evidence

ORD record
ord-b19d3cea05954ac985f6a224bcb440b8
Source dataset
uspto-grants-2003_07
Patent number
US06592884B2

Reaction notes

Loading…