Diisobutylaluminum hydride → (1-(2,6-dichlorophenyl)-4-isopropyl-1H-1,2,3-triazol-5-yl)methanol

HRID 424776Notes

Reaction equation

HRID 424776 reaction equation
C([O:3][C:4]([C:6]1[N:7]([C:14]2[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:21])[N:8]=[N:9][C:10]=1[CH:11]([CH3:13])[CH3:12])=O)C.CC(C[AlH]CC(C)C)C>C1COCC1.C1(C)C=CC=CC=1>[Cl:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[N:7]1[C:6]([CH2:4][OH:3])=[C:10]([CH:11]([CH3:13])[CH3:12])[N:9]=[N:8]1

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 667040591H-1,2,3-Triazole-5-carboxylic acid, 1-(2,6-dichlorophenyl)-4-(1-methylethyl)-, ethyl ester

Product 1

HCID 45790389(1-(2,6-dichlorophenyl)-4-isopropyl-1H-1,2,3-triazol-5-yl)methanolYield 90%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of 3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester (2.88 g) in THF (25 mL) is added 1 M DIBAL in toluene (38 mL). The reaction is allowed to warm to room temperature. Upon completion, the reaction mixture is quenched slowly with water and is acidified with 1 N HCl. The resulting solution is extracted two times with ethyl acetate. The combined organic layers are washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (2.26 g). ES/MS (m/e) 284 (M+0), 286 (M+2); mp: 154-155° C.

Workup

  1. customUpon completion, the reaction mixture is quenched slowly with water
  2. extractionThe resulting solution is extracted two times with ethyl acetate
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5e07a443fa8d44f09291bfc79eab7ead
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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