Dimethylformamide → HCID 86597655, compound

HRID 2213662Notes

Reaction equation

HRID 2213662 reaction equation
CN([CH:4]=[O:5])C.O=P(Cl)(Cl)Cl.[CH2:11]([O:13][C:14](=[O:24])[CH2:15][CH2:16][C:17](=[O:23])[C:18]1[CH:22]=[CH:21][NH:20][CH:19]=1)[CH3:12]>ClCCCl>[CH2:11]([O:13][C:14](=[O:24])[CH2:15][CH2:16][C:17](=[O:23])[C:18]1[CH:22]=[C:21]([CH:4]=[O:5])[NH:20][CH:19]=1)[CH3:12]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 10488085HCID 10488085, compound

Product 1

HCID 86597655HCID 86597655, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of DMF (1.2 mL) in 1,2-dichloroethane (25 mL) at 0° C. was treated with POCl3 (1.5 mL). The resulting solution was warmed to ambient temperature and then treated with a solution of γ-oxo-1-H-pyrrole-3-butanoic acid ethyl ester (2.06 g) in 1,2-dichloroethane (10 mL). The reaction mixture was heated to 55° C. After 3.5 hours, the reaction was quenched with the addition of 1N NaOH (16 mL), and then stirred overnight at ambient temperature. The reaction mixture was extracted with ethyl acetate (150 mL), and the organic layer was dried (MgSO4) and concentrated. The resulting oil was chromatographed on SiO2 (100 g) using 4:1 hexane/ethyl actetate to afford 5-formyl-γ-oxo-1-H-pyrrole-3-butanoic acid ethyl ester (0.54 g).

Workup

  1. temperatureThe reaction mixture was heated to 55° C
  2. customthe reaction was quenched with the addition of 1N NaOH (16 mL)
  3. extractionThe reaction mixture was extracted with ethyl acetate (150 mL)
  4. dry with materialthe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customThe resulting oil was chromatographed on SiO2 (100 g)

Sources & evidence

ORD record
ord-9635709f9b1c46cbb25b4c962093868d
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

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