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

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

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 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

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

Sources & evidence

ORD record: ord-e5db634352fa4d798eb663fcfaa7623b
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343990B2

Reaction notes

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