Sodium Hydroxide → HCID 21862857, compound

HRID 1415767Notes

Reaction equation

HRID 1415767 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[C:17]([C:19](OC)=[O:20])[CH:16]=[C:15]2[C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)=[CH:10][CH:9]=1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C(OCC)C.C(Cl)Cl.O>[F:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH:18]=[C:17]([CH2:19][OH:20])[CH:16]=[C:15]2[C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=2)=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 21862832HCID 21862832, compound

Product 1

HCID 21862857HCID 21862857, compoundYield 76.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

0.15 g (4.0 mmol) of lithium aluminum hydride was suspended in 25 ml of diethyl ether, and a solution of 0.98 g (2.6 mmol) of 1-(4-fluorophenyl)-4-methoxycarbonyl-2-(4-methylsulfonylphenyl)pyrrole [prepared as described in step (iii) above] in 20 ml of methylene chloride was added dropwise to the suspension whilst it was heated under reflux in a nitrogen atmosphere. The mixture was stirred under reflux for 1 hour, and then 0.15 ml of water, 0.15 ml of a 15% w/v aqueous solution of sodium hydroxide and 0.45 ml of water were added to the mixture, in that order. The mixture was then stirred at room temperature for 30 minutes. At the end of this time, the mixture was dehydrated by adding anhydrous magnesium sulfate, and it was filtered over a Celite (trade mark) filter aid. The solvent was then removed from the filtrate by distillation under reduced pressure. The residue was applied to a silica gel chromatography column and eluted with a 2:1 by volume mixture of ethyl acetate and hexane, to give 0.69 g (yield 76%) of the title compound as a white powder, melting at 88-90° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux in a nitrogen atmosphere
  3. temperatureunder reflux for 1 hour
  4. stirringThe mixture was then stirred at room temperature for 30 minutes
  5. filtrationwas filtered over a Celite (trade mark)
  6. filtrationfilter aid
  7. customThe solvent was then removed from the filtrate by distillation under reduced pressure
  8. washeluted with a 2:1 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-faa264a149554ec7ac8975f3b5514f18
Source dataset
uspto-grants-1999_06
Patent number
US05908858

Reaction notes

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