Water → 4-[4-(4-{2-[(e)-2-(-4-Trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1-trityl-1h-[1,2,3]triazole

HRID 750956Notes

Reaction equation

HRID 750956 reaction equation
[H-].[Na+].[C:3]([N:22]1[CH:26]=[C:25]([CH2:27][CH2:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)[N:24]=[N:23]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[CH2:39][C:40]1[N:41]=[C:42]([CH:45]=[CH:46][C:47]2[CH:52]=[CH:51][C:50]([S:53]([C:55]([F:58])([F:57])[F:56])=[O:54])=[CH:49][CH:48]=2)[O:43][CH:44]=1.O>CN(C)C=O>[F:58][C:55]([F:56])([F:57])[S:53]([C:50]1[CH:51]=[CH:52][C:47](/[CH:46]=[CH:45]/[C:42]2[O:43][CH:44]=[C:40]([CH2:39][O:37][C:34]3[CH:33]=[CH:32][C:31]([CH2:30][CH2:29][CH2:28][CH2:27][C:25]4[N:24]=[N:23][N:22]([C:3]([C:4]5[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=5)([C:16]5[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=5)[C:10]5[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=5)[CH:26]=4)=[CH:36][CH:35]=3)[N:41]=2)=[CH:48][CH:49]=1)=[O:54]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 236145474-{4-[1-(Triphenylmethyl)-1H-1,2,3-triazol-4-yl]butyl}phenolHCID 692923894-Chloromethyl-2-[2-(4-trifluoromethylsulfinyl-phenyl)-vinyl]-oxazole

Product 1

HCID 692919364-[4-(4-{2-[(e)-2-(-4-Trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-phenyl)-butyl]-1-trityl-1h-[1,2,3]triazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.1 mg (0.20 mmol) 95% sodium hydride were given at 0° C. to a solution of 90 mg (0.20 mmol) 4-[4-(1-trityl-1H-[1,2,3]triazol-4-yl)-butyl]-phenol in 3.0 ml N,N-dimethylformamide and stirred for 15 min. 66 mg (0.20 mmol) 4-chloromethyl-2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazole were added and stirring continued at 25° C. for 2 h. The reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was dried over sodium sulphate and the solvents distilled off in vacuo. Yield 146 mg.

Workup

  1. stirringstirring
  2. waitcontinued at 25° C. for 2 h
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. distillationthe solvents distilled off in vacuo

Sources & evidence

ORD record
ord-93c8c8de96684188bfa8bb4362c956cb
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

Loading…