Sodium borohydride → 1-{4-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenyl}-ethanol

HRID 424782Notes

Reaction equation

HRID 424782 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22](=[O:24])[CH3:23])=[C:18]([CH3:25])[CH:17]=2)=[C:12]([CH:26]([CH3:28])[CH3:27])[N:11]=[N:10]1.[BH4-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]([OH:24])[CH3:23])=[C:18]([CH3:25])[CH:17]=2)=[C:12]([CH:26]([CH3:28])[CH3:27])[N:11]=[N:10]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 667040541-{4-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenyl}-ethanone

Product 1

HCID 667041711-{4-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenyl}-ethanolYield 94.4%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a 0° C. solution of 1-{4-[3-(2,6-dichloro-phenyl)-5-isopropyl-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-phenyl}-ethanone (314 mg, 0.751 mmol) in THF/MeOH (6 mL/1 mL) is added sodium borohydride (116 mg, 3.04 mmol). The reaction is warmed to room temperature overnight. The reaction is concentrated and the residue is partitioned between EtOAc (100 mL) and 1 N HCl (20 mL). The aqueous layer is extracted with EtOAc (100 mL) and the combined organic layers are washed with brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue is purified via chromatography (40 g SiO2, 20% to 40% EtOAC/Hexanes) to yield the title compound (298 mg, 94%). LC-ES/MS m/e 419.7 (M+1).

Workup

  1. concentrationThe reaction is concentrated
  2. customthe residue is partitioned between EtOAc (100 mL) and 1 N HCl (20 mL)
  3. extractionThe aqueous layer is extracted with EtOAc (100 mL)
  4. washthe combined organic layers are washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified via chromatography (40 g SiO2, 20% to 40% EtOAC/Hexanes)

Sources & evidence

ORD record
ord-501e626bf2c449f99376af0b3479d191
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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