Ammonium Acetate → HCID 15010173, compound

HRID 1085607Notes

Reaction equation

HRID 1085607 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[Cl:14])[C:5]([CH2:7][CH2:8][CH:9]=O)=O.C([O-])(=O)C.[NH4+:19]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[NH:19][CH:9]=[CH:8][CH:7]=2)[CH:11]=[CH:12][C:13]=1[Cl:14]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 15753014HCID 15753014, compound

Product 1

HCID 15010173HCID 15010173, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 3-(3,4-dichlorobenzoyl) propionaldehyde (6 g, 26 mmol) in 60 mL of absolute ethanol is added ammonium acetate (4 g, 52 mmol). The reaction is refluxed for 20 minutes and allowed to cool. Most of the ethanol is rotary evaporated and 200 mL of 1:1 dichloromethane-diethyl ether along with 50 mL of water is added. The layers are separated and the organic phase is dried over sodium sulfate. Rotary evaporation yields a dark brown oil which is chromatographed over silica gel using 3:1 hexane-ethyl acetate as eluent to give the pyrrole (4.6 g, 83%) as a light brown solid, m.p. 49°-51° C.

Workup

  1. temperatureThe reaction is refluxed for 20 minutes
  2. temperatureto cool
  3. customMost of the ethanol is rotary evaporated
  4. addition200 mL of 1:1 dichloromethane-diethyl ether along with 50 mL of water is added
  5. customThe layers are separated
  6. dry with materialthe organic phase is dried over sodium sulfate
  7. customRotary evaporation
  8. customyields a dark brown oil which
  9. customis chromatographed over silica gel using 3:1 hexane-ethyl acetate as eluent

Sources & evidence

ORD record
ord-b3e1097c1d2f4147b47cce8342a3f3fe
Source dataset
uspto-grants-1991_04
Patent number
US05010098

Reaction notes

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