Trifluoroacetic acid → 3-(5-Methyl-1,3,4-oxadiazol-2-yl)phenol

HRID 1798801Notes

Reaction equation

HRID 1798801 reaction equation
COC1C=CC(C[O:8][C:9]2[CH:10]=[C:11]([C:15]3[O:16][C:17]([CH3:20])=[N:18][N:19]=3)[CH:12]=[CH:13][CH:14]=2)=CC=1.C(O)(C(F)(F)F)=O>>[CH3:20][C:17]1[O:16][C:15]([C:11]2[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][CH:12]=2)=[N:19][N:18]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58128485HCID 58128485, compound

Product 1

HCID 129617433-(5-Methyl-1,3,4-oxadiazol-2-yl)phenol

Procedure

2-{3-[(4-Methoxybenzyl)oxy]phenyl}-5-methyl-1,3,4-oxadiazole (100 mg, 0.338 mmol) was treated with 0.5 mL TFA and was stirred at room temperature for 10 min. Excess TFA was removed under vacuum and the residue was purified by column chromatography using a 24 gram biotage silica gel cartridge eluting with 20-50% ethyl acetate/hexanes (gradient) to give the product as white solid. LRMS calc: 176.1; obs: 177.2 (M+1).

Workup

  1. customExcess TFA was removed under vacuum
  2. customthe residue was purified by column chromatography
  3. washeluting with 20-50% ethyl acetate/hexanes (gradient)

Sources & evidence

ORD record
ord-e5db634352fa4d798eb663fcfaa7623b
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Reaction notes

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