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

HRID 2113866Notes

Reaction equation

HRID 2113866 reaction equation
[H-].[Na+].[N:3]1([CH2:8][CH2:9][O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[CH:7]=[CH:6][N:5]=[N:4]1.Cl[CH2:20][C:21]1[N:22]=[C:23]([CH:26]=[CH:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH:35]([F:37])[F:36])=[CH:30][CH:29]=2)[O:24][CH:25]=1.O>CN(C=O)C>[F:37][CH:35]([F:36])[O:34][C:31]1[CH:32]=[CH:33][C:28](/[CH:27]=[CH:26]/[C:23]2[O:24][CH:25]=[C:21]([CH2:20][O:18][C:15]3[CH:14]=[CH:13][C:12]([CH2:11][O:10][CH2:9][CH2:8][N:3]4[CH:7]=[CH:6][N:5]=[N:4]4)=[CH:17][CH:16]=3)[N:22]=2)=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 210758954-(2-[1,2,3]Triazol-1-yl-ethoxymethyl)-phenolHCID 691125744-(Chloromethyl)-2-{2-[4-(difluoromethoxy)phenyl]ethenyl}-1,3-oxazole

Product 1

HCID 112135201-[2-(4-{2-[2-(E)-(4-Difluoromethoxy-phenyl)-vinyl]-oxazol-4-ylmethoxy}-benzyloxy)-ethyl]-1H-[1,2,3]triazoleYield 60.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

23 mg (0.91 mmol) 95% Sodium hydride were given to a solution of 200 mg (0.91 mmol) 4-(2-[1,2,3]triazol-1-yl-ethoxymethyl)-phenol in 5.0 ml DMF and stirred for 15 min. 260 mg (0.91 mmol) 4-chloromethyl-2-[2-(4-difluoromethoxy-phenyl)-vinyl]-oxazole were added and stirring continued at r.t. for 12 h. After addition of 20 ml water the resulting precipitate was collected, washed with water (2×10 ml), methanol/water 1:1 (2×10 ml), a small amount of diethyl ether and dried in vacuo at 40° C. to yield 256 mg (60%) of the product as beige powder.

Workup

  1. stirringstirring
  2. waitcontinued at r.t. for 12 h
  3. customwas collected
  4. washwashed with water (2×10 ml), methanol/water 1:1 (2×10 ml)
  5. dry with materiala small amount of diethyl ether and dried in vacuo at 40° C.

Sources & evidence

ORD record
ord-c9f6274b14e54eeebaddb2ba81e51cd4
Source dataset
uspto-grants-2008_10
Patent number
US07432291B2

Reaction notes

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