(2-fluoro-5-(2-methyl-1,3-dioxolan-2-yl)phenyl)(2-methyl-5-phenyl-2H-1,2,4-triazol-3-yl)methanol → 1-(4-fluoro-3-(hydroxy(2-methyl-5-phenyl-2H-1,2,4-triazol-3-yl)methyl)phenyl)ethanone

HRID 2105085Notes

Reaction equation

HRID 2105085 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:13])OCC[O:9]2)=[CH:4][C:3]=1[CH:14]([C:16]1[N:17]([CH3:27])[N:18]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:20]=1)[OH:15]>CC(C)=O.C(O)(=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:9])[CH3:13])=[CH:4][C:3]=1[CH:14]([OH:15])[C:16]1[N:17]([CH3:27])[N:18]=[C:19]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:20]=1

Participants

3

Reactant 1

HCID 57803748(2-fluoro-5-(2-methyl-1,3-dioxolan-2-yl)phenyl)(2-methyl-5-phenyl-2H-1,2,4-triazol-3-yl)methanol

Product 1

HCID 578036451-(4-fluoro-3-(hydroxy(2-methyl-5-phenyl-2H-1,2,4-triazol-3-yl)methyl)phenyl)ethanoneYield 131.1%

Reagents, catalysts & solvents 1

HCID 86607946Acetone Acetic Acid H2OSolvent

Procedure

Intermediate 416.3 (500 mg, 1.36 mmol) was heated in a solution of Acetone:Acetic Acid:H2O (2:1:1, 8 mL) at 125° C. for 30 min using a PC microwave. The reaction product was then concentrated and purified by flash chromatography (0 to 100% EtOAc/hexanes gradient) to afford 580 mg of Intermediate 416.4. LCMS (2 min gradient) RT=1.59 min, 326.31 (M+H)+.

Workup

  1. concentrationThe reaction product was then concentrated
  2. custompurified by flash chromatography (0 to 100% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-c1fe8299016b4f30a4a15d40e30ca123
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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