Ethyl ketone → ethyl 5-(4,5-dimethoxy-2-nitrobenzoyl)-2-(3-methoxypentan-3-yl)-2H-1,2,3-triazole-4-carboxylate
Reaction equation
O.[C:2]1(C)[CH:7]=[CH:6]C(S(O)(=O)=O)=[CH:4][CH:3]=1.CC[C:15](=[O:18])CC.COC(OC)OC.[CH3:26][O:27][C:28]1[C:45]([O:46][CH3:47])=[CH:44][C:31]([C:32]([C:34]2[NH:38][N:37]=[N:36][C:35]=2[C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:33])=[C:30]([N+:48]([O-:50])=[O:49])[CH:29]=1>C(Cl)Cl.C(N(CC)CC)C>[CH3:26][O:27][C:28]1[C:45]([O:46][CH3:47])=[CH:44][C:31]([C:32]([C:34]2[C:35]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[N:36][N:37]([C:2]([O:18][CH3:15])([CH2:7][CH3:6])[CH2:3][CH3:4])[N:38]=2)=[O:33])=[C:30]([N+:48]([O-:50])=[O:49])[CH:29]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
p-Toluenesulfonic acid monohydrate (20 mg) was added to a solution of 3-pentanone (3.1 ml) and trimethylorthoformate (3.3 ml) in methylene chloride (10 ml). The mixture was heated for one hr with stirring. This solution (4 ml) was added to a solution of ethyl 5-(4,5-dimethoxy-2-nitrobenzoyl)-1H-1,2,3-triazole-4-carboxylate (Synthesis Example 2) (140 mg) in methylene chloride (2 ml). The mixture was stirred at room temperature for one hr, and triethylamine (0.05 ml) was then added thereto. The mixture was post-treated by a conventional method and subjected to separation and purification to give ethyl 5-(4,5-dimethoxy-2-nitrobenzoyl)-2-(3-methoxypentan-3-yl)-2H-1,2,3-triazole-4-carboxylate (140 mg, 78%) as a yellow powder.
Workup
- temperatureThe mixture was heated for one hr
- stirringThe mixture was stirred at room temperature for one hr
- additionThe mixture was post-treated by a conventional method
- customsubjected to separation and purification
Sources & evidence
- ORD record
- ord-7b8a9c13603c44a9bd7b3da3c37c8d82
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07022860B2
Reaction notes
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