Water → HCID 15572314, compound

HRID 2286528Notes

Reaction equation

HRID 2286528 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]2[C:14]([C:24](OCC)=O)=[CH:15][NH:16][C:17]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[OH-].[Na+]>C1COCC1>[C:18]1([C:17]2[NH:16][CH:15]=[C:14]([CH3:24])[C:13]=2[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 10379523HCID 10379523, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15572314HCID 15572314, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred slurry of 0.76 g (20 mmoles) of lithium aluminum hydride in 25 ml THF was added dropwise a solution of 0.58 g (2 mmoles) of ethyl 4,5-diphenylpyrrole-3-carboxylate in 5 ml THF. The mixture was heated at reflux overnight. After cooling, 0.8 ml water, 2.4 ml 15% sodium hydroxide solution and 0.8 ml water were added dropwise. The solids were removed by filtration and the filtrate concentrated by rotary evaporation. The crystalline residue was purified by chromatography on 50 g silicic acid (CC-7) eluting with hexane/toluene (90/10) to give 0.25 g of product, m.p. 163°-164° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. customThe solids were removed by filtration
  5. concentrationthe filtrate concentrated by rotary evaporation
  6. customThe crystalline residue was purified by chromatography on 50 g silicic acid (CC-7)
  7. washeluting with hexane/toluene (90/10)

Sources & evidence

ORD record
ord-4235c3b9cc924ac2bfb0ef698763d53d
Source dataset
uspto-grants-1981_05
Patent number
US04267190

Reaction notes

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