Diisobutylaluminum hydride → [3-(2,6-Dichloro-phenyl)-5-trifluoromethyl-3H-[1,2,3]triazol-4-yl]methanol

HRID 424811Notes

Reaction equation

HRID 424811 reaction equation
C([O:3][C:4]([C:6]1[N:7]([C:15]2[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:22])[N:8]=[N:9][C:10]=1[C:11]([F:14])([F:13])[F:12])=O)C.CC(C[AlH]CC(C)C)C>C1COCC1>[Cl:22][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([Cl:21])[C:15]=1[N:7]1[C:6]([CH2:4][OH:3])=[C:10]([C:11]([F:13])([F:14])[F:12])[N:9]=[N:8]1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 667041363-(2,6-Dichloro-phenyl)-5-trifluoromethyl-3H-[1,2,3]triazole-4-carboxylic Acid Ethyl Ester

Product 1

HCID 66704107[3-(2,6-Dichloro-phenyl)-5-trifluoromethyl-3H-[1,2,3]triazol-4-yl]methanolYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of 3-(2,6-dichloro-phenyl)-5-trifluoromethyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester (28 g, 79 mmol) in THF (200 mL) is added dropwise 1M DIBAL (166 mL, 166 mmol) keeping the temperature below 5° C. After the addition, the bath is removed and the reaction is stirred for 18 h. The reaction is cooled to 0° C. and ether (300 mL) is added. The reaction is quenched with 1N HCl (250 mL) dropwise keeping the temperature below 15° C. The layers are separated and the water layer is washed with Ether (100 mL). The organics are combined and washed with water, brine, and dried with Na2SO4. The organic layer is concentrated to dryness to yield the title compound (24 g, 97%) and is used with no further purification. ES/MS m/e 312.0 (M+1).

Workup

  1. customthe temperature below 5° C
  2. additionAfter the addition
  3. customthe bath is removed
  4. additionether (300 mL) is added
  5. customThe reaction is quenched with 1N HCl (250 mL)
  6. customthe temperature below 15° C
  7. customThe layers are separated
  8. washthe water layer is washed with Ether (100 mL)
  9. washwashed with water, brine
  10. dry with materialdried with Na2SO4
  11. concentrationThe organic layer is concentrated to dryness

Sources & evidence

ORD record
ord-facd9dea1d8c4a30ba9985adbcb35e4a
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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