Sodium hydride → 5-(2,6-Dimethoxyphenyl)-4-(4-(trifluoromethoxy)benzyl)-morpholin-3-one
Reaction equation
[H-].[Na+].Cl[CH2:4][C:5]([N:7]([CH:20]([C:23]1[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=1[O:31][CH3:32])[CH2:21][OH:22])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=1)=[O:6]>CN(C=O)C>[CH3:32][O:31][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([O:29][CH3:30])[C:23]=1[CH:20]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)[C:5](=[O:6])[CH2:4][O:22][CH2:21]1Participants
4
Procedure
A cooled (−25° C.) mixture of NaH (60% dispersion in mineral oil; 1 mg; 0.025 mmol) in anh. DMF (1 ml) was treated dropwise with a solution of 2-chloro-N-(1-(2,6-dimethoxyphenyl)-2-hydroxyethyl)-N-(4-(trifluoromethoxy)benzyl)acetamide (10 mg; 0.022 mmol) in anh. DMF (1 ml). The resulting mixture was further stirred at rt, under nitrogen, for 30 min. The mixture was then filtered, and the obtained filtrate was directly purified by preparative HPLC affording 5-(2,6-dimethoxyphenyl)-4-(4-(trifluoromethoxy)benzyl)-morpholin-3-one as a yellow oil. LC-MS (conditions E): tR=0.79 min.; [M+H]+: 412.06 g/mol.