Hydrochloric Acid → HCID 86601208, compound

HRID 349254Notes

Reaction equation

HRID 349254 reaction equation
[BH4-].[Na+].C([O:5][C:6]([C:8]1[N:9]=[N:10][N:11]([CH2:19][C:20]2[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:21]=2)[C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O)C.Cl.C(Cl)Cl>CCO>[F:33][C:30]([F:31])([F:32])[C:22]1[CH:21]=[C:20]([CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=1)[CH2:19][N:11]1[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:8]([CH2:6][OH:5])[N:9]=[N:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 86601209HCID 86601209, compound

Product 1

HCID 86601208HCID 86601208, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add sodium borohydride (1.70 g, 0.045 mol) to a solution of 1-(3,5-bis-trifluoromethylbenzyl)-5-phenyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester (5.0 g, 0.011 mol) in EtOH (70 mL) and heat the mixture to reflux. After 2 h, cool to RT and add the reaction mixture to 0.5 N HCl (200 mL) and methylene chloride (200 mL). Separate the layers and extract the aqueous layer with methylene chloride (50 mL). Dry the combined organic layers over MgSO4, filter, and concentrate to give [1-(3,5-bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazol-4-yl]-methanol.

Workup

  1. temperatureheat the mixture
  2. temperatureto reflux
  3. customSeparate the layers
  4. extractionextract the aqueous layer with methylene chloride (50 mL)
  5. dry with materialDry the combined organic layers over MgSO4
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-286f18e3a7b34d54b9c8a1b891d25b2d
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Reaction notes

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