Trimethyl orthoformate → HCID 59556706, compound

HRID 1172968Notes

Reaction equation

HRID 1172968 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:24]=[CH:23][C:20](C=O)=[CH:19][CH:18]=3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:37]([O:42][CH3:43])([O:40][CH3:41])OC>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:12]2[N:16]=[C:15]([C:17]3[CH:24]=[CH:23][C:20]([CH:37]([O:40][CH3:41])[O:42][CH3:43])=[CH:19][CH:18]=3)[O:14][N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 59556690HCID 59556690, compound

Product 1

HCID 59556706HCID 59556706, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(3-(3-bromo-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzaldehyde (0.551 g, 1.423 mmol), molecular sieve (4A, 8-12 mesh, 130 mg) and p-toluenesulfonic acid monohydrate (0.037 g, 0.195 mmol) were added in trimethyl orthoformate (4 ml, 36.2 mmol) and methanol (6 ml), the reaction mixture was heated at 80° C. for 16 hr. The solution was cooled, the reaction mixture was concentrated to afford grey solid, which was purified via silica gel chromatography (12 g, 20% EtOAc:Heptane) to afford 3-(3-bromo-4-isopropoxyphenyl)-5-(4-(dimethoxymethyl)phenyl)-1,2,4-oxadiazole (0.61 g, 1.366 mmol, 96% yield) as white solid.

Workup

  1. temperatureThe solution was cooled
  2. concentrationthe reaction mixture was concentrated
  3. customto afford grey solid, which
  4. customwas purified via silica gel chromatography (12 g, 20% EtOAc:Heptane)

Sources & evidence

ORD record
ord-bc3b39ea1fe742c5a4dc238bdcb62bf0
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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