Potassium Iodide → 1-[2-(4-{2-[2-(4-Difluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-2-methyl-benzyloxy)-ethyl]-1H-[1,2,3]triazole

HRID 2113887Notes

Reaction equation

HRID 2113887 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:17])[CH:5]=[CH:6][C:7]=1[CH2:8][O:9][CH2:10][CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[N:13]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:25][C:26]1[N:27]=[C:28]([CH:31]=[CH:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH:40]([F:42])[F:41])=[CH:35][CH:34]=2)[O:29][CH:30]=1.[I-].[K+]>CC(=O)CC>[F:42][CH:40]([F:41])[O:39][C:36]1[CH:37]=[CH:38][C:33]([CH:32]=[CH:31][C:28]2[O:29][CH:30]=[C:26]([CH2:25][O:17][C:4]3[CH:5]=[CH:6][C:7]([CH2:8][O:9][CH2:10][CH2:11][N:12]4[CH:16]=[CH:15][N:14]=[N:13]4)=[C:2]([CH3:1])[CH:3]=3)[N:27]=2)=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 691125744-(Chloromethyl)-2-{2-[4-(difluoromethoxy)phenyl]ethenyl}-1,3-oxazoleHCID 692910153-Methyl-4-(2-[1,2,3]triazol-1-yl-ethoxymethyl)-phenol

Product 1

HCID 692923021-[2-(4-{2-[2-(4-Difluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-2-methyl-benzyloxy)-ethyl]-1H-[1,2,3]triazoleYield 59%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 201 mg (0.86 mmol) 3-methyl-4-(2-[1,2,3]triazol-1-yl-ethoxymethyl)-phenol and 169 mg (0.52 mmol) cesium carbonate in 10 ml 2-butanone was stirred at 60° C. for 30 minutes, then 246 mg (0.86 mmol) 4-chloromethyl-2-[2-(4-difluoromethoxy-phenyl)-vinyl]-oxazole and 143 mg (0.86 mmol) potassium iodide were added and stirring was continued overnight. After evaporation, the residue was mixed with aqueous NaOH (1N) and extracted with ethyl acetate. The combined extracts were dried, evaporated and the product purified on silica (ethyl acetate) to yield 242 mg (59%) 1-[2-(4-{2-[2-(4-Difluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-2-methyl-benzyloxy)-ethyl]-1H-[1,2,3]triazole as a white solid melting at 119-120° C.

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. customAfter evaporation
  4. additionthe residue was mixed with aqueous NaOH (1N)
  5. extractionextracted with ethyl acetate
  6. customThe combined extracts were dried
  7. customevaporated
  8. customthe product purified on silica (ethyl acetate)

Sources & evidence

ORD record
ord-012e593257834491b8ef65f02f9e5a91
Source dataset
uspto-grants-2008_10
Patent number
US07432291B2

Reaction notes

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