Methanol → HCID 43328690, compound

HRID 571865Notes

Reaction equation

HRID 571865 reaction equation
[F:1][CH:2]([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[C:13]([C:15]([O:17]CC)=[O:16])[N:12]=[N:11]2)=[CH:6][CH:5]=1.CO.O.O.[OH-].[Li+]>C1COCC1>[F:20][CH:2]([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[N:12]=[N:11]2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 71086828HCID 71086828, compound

Product 1

HCID 43328690HCID 43328690, compoundYield 107.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of ethyl 1-(4-(difluoromethoxy)phenyl)-1H-1,2,3-triazole-4-carboxylate (600 mg, 2.12 mmol) in a mixture of THF (7 ml), methanol (7 ml) and water (7 ml) was added lithium hydroxide hydrate (267 mg, 6.36 mmol). The solution was heated to 70° C. for 3 h. Most of the organic solvent was removed under reduced pressure. Water was added and the solution was extracted with methyl tert-butyl ether to remove non-acid material. Then 25% aq. hydrochloric acid was added to reach acidic pH. The product precipitated and the mixture was extracted three times with ethyl acetate. The organic layers were combined, dried (MgSO4) and evaporated to yield a light yellow solid (583 mg, 99%). MS (ISP): 253.9 ([M−H]+); 509.2 ([2M−H]+).

Workup

  1. customMost of the organic solvent was removed under reduced pressure
  2. additionWater was added
  3. extractionthe solution was extracted with methyl tert-butyl ether
  4. customto remove non-acid material
  5. additionThen 25% aq. hydrochloric acid was added
  6. customThe product precipitated
  7. extractionthe mixture was extracted three times with ethyl acetate
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-99a7e95ad71043fb9146befc507b9be8
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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