Sodium Hydroxide → (E)-3-[3-(4-Fluorophenyl)-5-isopropyl-2-phenyl-1-(1-pyrrolidinyl)-pyrrol-4-yl]-prop-2-enal

HRID 704745Notes

Reaction equation

HRID 704745 reaction equation
CN(C)[CH:3]=[CH:4][CH:5]=[O:6].P(Cl)(Cl)(Cl)=O.[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:24]=[C:23]([CH:25]([CH3:27])[CH3:26])[N:22]([N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[C:21]=2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:16][CH:15]=1.[OH-].[Na+]>C(#N)C.O1CCCC1.C1(C)C=CC=CC=1.O>[F:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[C:24](/[CH:3]=[CH:4]/[CH:5]=[O:6])=[C:23]([CH:25]([CH3:27])[CH3:26])[N:22]([N:28]3[CH2:29][CH2:30][CH2:31][CH2:32]3)[C:21]=2[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[CH:18][CH:19]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 791253-(Dimethylamino)-2-propenalHCID 145787423-(4-Fluorophenyl)-5-isopropyl-2-phenyl-1-(1-pyrrolidinyl)pyrrole

Product 1

HCID 14578743(E)-3-[3-(4-Fluorophenyl)-5-isopropyl-2-phenyl-1-(1-pyrrolidinyl)-pyrrol-4-yl]-prop-2-enal

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolvent3×HCID 8028TetrahydrofuranSolventHCID 22272177Toluene waterSolvent

Procedure

1.9 g (17.9 mmol) of 90% strength 3-dimethylaminoacrolein in 30 ml of acetonitrile AR are added dropwise under nitrogen to 1.8 ml (19.2 mmol) of freshly distilled phosphorus oxychloride in 20 ml of acetonitrile AR at -5° C. The mixture is subsequently stirred for 10 minutes and 2.3 g (6.4 mmol) of the compound from Example 3 dissolved in 20 ml of acetonitrile AR and 30 ml of tetrahydrofuran AR are then added dropwise at the same temperature. The mixture is subsequently heated to reflux overnight and cooled to room temperature. The batch is added to a mixture of 4.7 g of sodium hydroxide in 300 ml of toluene/water 1:1 in such a way that the temperature does not exceed 10° C. The mixture is subsequently stirred for 10 minutes, the organic phase is separated off and the aqueous phase is extracted twice using ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution and dried over magnesium sulphate. After concentrating in vacuo, the residue is stirred with ethyl acetate/petroleum ether 1:1, filtered off with suction and dried in a desiccator.

Workup

  1. additionare then added dropwise at the same temperature
  2. temperatureThe mixture is subsequently heated
  3. temperatureto reflux overnight
  4. customdoes not exceed 10° C
  5. stirringThe mixture is subsequently stirred for 10 minutes
  6. customthe organic phase is separated off
  7. extractionthe aqueous phase is extracted twice using ethyl acetate
  8. washwashed with saturated sodium chloride solution
  9. dry with materialdried over magnesium sulphate
  10. concentrationAfter concentrating in vacuo
  11. stirringthe residue is stirred with ethyl acetate/petroleum ether 1:1
  12. filtrationfiltered off with suction
  13. customdried in a desiccator

Sources & evidence

ORD record
ord-37280f87ded04a4c8b73e759e70e0b54
Source dataset
uspto-grants-1991_01
Patent number
US04988711

Reaction notes

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