Water → 1-[2-(2-fluoro-4-{2-[2-(E)-(4-trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-benzyloxy)-ethyl]-1H-[1,2,3]triazole

HRID 2113893Notes

Reaction equation

HRID 2113893 reaction equation
[F: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.[H-].[Na+].Cl[CH2:21][C:22]1[N:23]=[C:24]([CH:27]=[CH:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][C:36]([F:39])([F:38])[F:37])=[CH:31][CH:30]=2)[O:25][CH:26]=1.O>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([O:17][CH2:21][C:22]2[N:23]=[C:24](/[CH:27]=[CH:28]/[C:29]3[CH:30]=[CH:31][C:32]([O:35][C:36]([F:39])([F:37])[F:38])=[CH:33][CH:34]=3)[O:25][CH:26]=2)[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

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 690715774-Chloromethyl-2-[2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazoleHCID 692922963-Fluoro-4-(2-[1,2,3]triazol-1-yl-ethoxymethyl)-phenol

Product 1

HCID 112606231-[2-(2-fluoro-4-{2-[2-(E)-(4-trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-benzyloxy)-ethyl]-1H-[1,2,3]triazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 201 mg (0.847 mmol) 3-Fluoro-4-(2-[1,2,3]triazol-1-yl-ethoxylmethyl)-phenol in 5 ml dimethylformamide was treated with 22.5 mg ( 0.890 mmol) 95% sodium hydride and stirred at room temperature for 20 min, then 257 mg (0.847 mmol) 4-chloromethyl-2-[2-(4-trifluoromethoxy-phenyl)-vinyl]-oxazole were added and stirring continued for 14 h. After addition of water, the precipitate was isolated, washed thoroughly with water, twice with ether and dried to give 1-[2-(2-fluoro-4-{2-[2-(E)-(4-trifluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-benzyloxy)-ethyl]-1H-[1,2,3]triazole.

Workup

  1. stirringstirring
  2. waitcontinued for 14 h
  3. customthe precipitate was isolated
  4. washwashed thoroughly with water, twice with ether
  5. customdried

Sources & evidence

ORD record
ord-4e239b2cfc0b4bbd99219270c6fe11a2
Source dataset
uspto-grants-2008_10
Patent number
US07432291B2

Reaction notes

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