Dimethylformamide → HCID 86743527, compound

HRID 1639279Notes

Reaction equation

HRID 1639279 reaction equation
[CH3:1][O:2]/[CH:3]=[C:4](\[N:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1)/[C:5]([O:7][CH3:8])=[O:6].P(Cl)(Cl)(Cl)=O.CN([CH:22]=[O:23])C.C([O-])(=O)C.[Na+]>ClCCCl>[CH3:1][O:2]/[CH:3]=[C:4](\[N:9]1[CH:10]=[CH:11][CH:12]=[C:13]1[CH:22]=[O:23])/[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 13786949HCID 13786949, compound

Product 1

HCID 86743527HCID 86743527, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of (Z)-methyl 3-methoxy-2-(pyrrol-1-yl)acrylate (10 g, 0.055 mol) in 1,2-dichloroethane (25 ml) was added dropwise with stirring at room temperature to the mixture resulting from adding phosphoryl chloride (5.6 ml, 0.06 mol) to DMF (4.7 ml, 0.06 mol) while cooling in ice. After stirring for 3 hours at room temperature, a saturated aqueous solution of sodium acetate (100 ml) was added and the resulting mixture was heated at reflux for 30 minutes. The mixture was cooled then extracted with dichloromethane (2×150 ml). The extracts were washed with water, dried and concentrated to give a clear oil (11.7 g, of a mixture of the 2 and 3-formylated pyrrole) which was purified by HPLC on silica gel using diethyl ether as the eluant to give (Z)-methyl 3-methoxy-2-(2-formylpyrrol-1-yl)acrylate (5.7 g, 45%) as a white crystalline solid, m.p. 58°-9° C., proton n.m.r. (CDCl3) delta: 3.74 (3) s, 3.88 (3) s, 6.35 (1) m, 6.87 (1) m, 7.04 (1) m, 7.55 (1) s, 9.30 (1) d.

Workup

  1. customresulting
  2. temperaturewhile cooling in ice
  3. stirringAfter stirring for 3 hours at room temperature
  4. temperaturethe resulting mixture was heated
  5. temperatureat reflux for 30 minutes
  6. temperatureThe mixture was cooled
  7. extractionthen extracted with dichloromethane (2×150 ml)
  8. washThe extracts were washed with water
  9. customdried
  10. concentrationconcentrated
  11. customto give a clear oil (11.7 g
  12. customwas purified by HPLC on silica gel

Sources & evidence

ORD record
ord-188afcf821df4ba2a0ee9760b04b0c57
Source dataset
uspto-grants-1989_11
Patent number
US04883807

Reaction notes

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