Hydrochloric Acid → HCID 23324900, compound

HRID 1380916Notes

Reaction equation

HRID 1380916 reaction equation
[OH:1][C:2]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)([C:9](=[O:17])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[CH2:3][N:4]1[CH:8]=[N:7][CH:6]=[N:5]1.[BH4-].[Na+].Cl>C(O)(C)C>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:2]([OH:1])([CH:9]([OH:17])[C:10]([F:15])([F:16])[C:11]([F:14])([F:13])[F:12])[CH2:3][N:4]2[CH:8]=[N:7][CH:6]=[N:5]2)=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 23324899HCID 23324899, compound

Product 1

HCID 23324900HCID 23324900, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-Hydroxy-2-(4-fluorophenyl)-4,4,5,5,5-pentafluoro-1-(1H-1,2,4-triazol-1-yl)pentan-3-one (0.2 g., 0.00057M) was dissolved in isopropyl alcohol (10 ml.) and the resulting solution was cooled in ice. Sodium borohydride (0.2 g., 0.005M) was then added, and the mixture was stirred for 1 hour whilst being cooled in an ice bath. Hydrochloric acid (2N, 10 ml.) was then added. The isopropyl alcohol was evaporated, the remaining solution was treated with dilute aqueous sodium bicarbonate solution to neutrality, and the mixture was extracted with methylene chloride (3×10 ml). The combined methylene chloride extracts were dried (MgSO4) and evaporated. Chromatography of the residue on silica (230-400 mesh) using ethyl acetate as the eluant gave the pure title compound, 0.09 g., which was then recrystallised from ethyl acetate/60°-80° petrol, m.p. (after said recrystallisation) 165°-168°.

Workup

  1. temperaturethe resulting solution was cooled in ice
  2. temperaturewhilst being cooled in an ice bath
  3. customThe isopropyl alcohol was evaporated
  4. additionthe remaining solution was treated with dilute aqueous sodium bicarbonate solution to neutrality
  5. extractionthe mixture was extracted with methylene chloride (3×10 ml)
  6. dry with materialThe combined methylene chloride extracts were dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-1860494479cb4302ac9a11fbca3d36d6
Source dataset
uspto-grants-1986_04
Patent number
US04584307

Reaction notes

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