Cesium hydroxide → 2-(4-Fluorophenyl)-5-methyl4-[cis-3-(2-nitrobenzyloxy)cyclohexyloxymethyl]oxazole
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:22])=[C:11]([CH2:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH:17]([OH:21])[CH2:16]3)[N:12]=2)=[CH:4][CH:3]=1.[N+:23]([C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH2:28]Br)([O-:25])=[O:24].[OH-].[Cs+]>C(#N)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]([CH3:22])=[C:11]([CH2:13][O:14][C@H:15]3[CH2:20][CH2:19][CH2:18][C@@H:17]([O:21][CH2:28][C:27]4[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=4[N+:23]([O-:25])=[O:24])[CH2:16]3)[N:12]=2)=[CH:6][CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
0.1 g of 3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexanol is dissolved in 3 ml of acetonitrile, and 0.21 g of 2-nitrobenzyl bromide and 0.36 g of tetrabutylammonium iodide are added. 0.57 ml of cesium hydroxide solution (50% strength solution in water) is added dropwise, and the two-phase mixture is stirred vigorously at room temperature, for 12 hours. The reaction is checked (LCMS), showing the formation of the desired product, in addition to unreacted alcohol 3-[2-(4-fluorophenyl)-5-methyloxazol4-ylmethoxy]cyclohexanol. By addition of a further 0.2 g of 2-nitrobenzyl bromide (2 eq) at room temperature and stirring at room temperature for a further 12 hours, the reaction is terminated by addition of 2 ml of 1N hydrochloric acid and the mixture is extracted with ethyl acetate (2×10 ml). The combined organic phases are washed with saturated sodium chloride solution and dried over magnesium sulfate. Purification by HPLC gives 0.05 g of the compound 2-(4-fluorophenyl)-5-methyl4-[cis-3-(2-nitrobenzyloxy)cyclohexyloxymethyl]oxazole as a clear colorless oil.
Sources & evidence
- ORD record
- ord-ce43b7328e02487f9e4760e44de24f01
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07148246B2
Reaction notes
Loading…