Water → {1-[(3,4-Dichlorophenyl)methyl]-1H-1,2,3-triazol-4-yl}methanol

HRID 222370Notes

Reaction equation

HRID 222370 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[CH:14]=[C:13]([C:15](OCC)=[O:16])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].CC(C[AlH]CC(C)C)C.[NH4+].[Cl-].O>C1COCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[CH:14]=[C:13]([CH2:15][OH:16])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 962WaterHCID 14487Diisobutylaluminum hydride2×HCID 25517Ammonium ChlorideHCID 59583668Ethyl 1-[(3,4-dichlorophenyl)methyl]-1H-1,2,3-triazole-4-carboxylate2×

Product 1

HCID 59583661{1-[(3,4-Dichlorophenyl)methyl]-1H-1,2,3-triazol-4-yl}methanol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-[(3,4-dichlorophenyl)methyl]-1H-1,2,3-triazole-4-carboxylate (Intermediate 10) (0.33 g, 1.09 mmol) in THF was added a 1M solution of DIBAL-H in toluene (2.3 mL, 2.1 eq) and the reaction was stirred at room temperature for 2 hours. The reaction was not completed. Two more equivalents of a 1M solution of DIBAL-H in toluene were added and the reaction was stirred for a further 18 hours. Solid NH4Cl was added followed by water and the aqueous phase was extracted with ether, ethyl acetate, dried over sodium sulphate and evaporated. The title compound was obtained as a white powder after recrystallisation from isopropyl ether (170 mg, 60%). LC/MS: m/z 258 (M+H)+ Rt: 2.45 min.

Workup

  1. stirringthe reaction was stirred for a further 18 hours
  2. extractionthe aqueous phase was extracted with ether, ethyl acetate
  3. dry with materialdried over sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-efeca2dbc8294417bf15836d54fa7292
Source dataset
uspto-grants-2012_06
Patent number
US08207204B2

Reaction notes

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