p-Toluenesulfonic acid → 2-[(Benzyloxy)methyl]-1,3,4-oxadiazole

HRID 512005Notes

Reaction equation

HRID 512005 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([NH:12][NH2:13])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:14](OC)(OC)OC.CC1C=CC(S(O)(=O)=O)=CC=1>>[CH2:1]([O:8][CH2:9][C:10]1[O:11][CH:14]=[N:13][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 224803422-(Benzyloxy)acetohydrazide

Product 1

HCID 579994412-[(Benzyloxy)methyl]-1,3,4-oxadiazoleYield 49%

Procedure

To a mixture of 71, (2.7 g, 15 mmol) and trimethyl orthoformate (5 mL) was added p-TSA, (anhydrous, 255 mg, 1.5 mmol). The mixture was refluxed for 3 h and the excess trimethyl orthoformate evaporated under reduced pressure. The crude product was purified over a column of silica gel, eluting with 30% acetone-petroleum ether to give 72 as a colorless liquid (1.4 g), in 49% yield (two steps). 1H NMR (500 MHz, CDCl3) δ 8.43 (s, 1H), 7.39-7.31 (m, 5H), 4.77 (s, 2H), 4.64 (s, 2H).

Workup

  1. temperatureThe mixture was refluxed for 3 h
  2. customthe excess trimethyl orthoformate evaporated under reduced pressure
  3. customThe crude product was purified over a column of silica gel
  4. washeluting with 30% acetone-petroleum ether

Sources & evidence

ORD record
ord-c70ec6072de14381b2a42dd133e94653
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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