Hydrochloric Acid → HCID 13371360, compound

HRID 2412952Notes

Reaction equation

HRID 2412952 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([C:22](=[O:27])[C:23]([F:26])([F:25])[F:24])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.C(O)C.[BH4-].[Na+].Cl>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([CH:22]([C:23]([F:26])([F:25])[F:24])[OH:27])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 15572342HCID 15572342, compound

Product 1

HCID 13371360HCID 13371360, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 1.9 g (0.005 mole) of 1-[4,5-bis(4-methoxyphenyl)-1H-pyrrol-2-yl]-2,2,2-trifluoro-1-ethanone and 25 ml ethanol at 0° was added 0.4 g (0.01 mole) of sodium borohydride all at once. The mixture was stirred at 0° 0.5 hour, then at room temperature 1 hour. The mixture was chilled in an ice bath and 40 ml of 1N hydrochloric acid was added dropwise. The mixture was poured into water and extracted with methylene chloride. The organic layers were dried and concentrated. The crude solid was triturated with methylcyclohexane and collected to give 1.6 g of product, m.p. 84°-86°.

Workup

  1. customat room temperature
  2. custom1 hour
  3. temperatureThe mixture was chilled in an ice bath
  4. extractionextracted with methylene chloride
  5. customThe organic layers were dried
  6. concentrationconcentrated
  7. customThe crude solid was triturated with methylcyclohexane
  8. customcollected

Sources & evidence

ORD record
ord-9de1d93a325440378f0743dd874aec27
Source dataset
uspto-grants-1985_01
Patent number
US04495196

Reaction notes

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