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.C(OC)(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 trimethyl orthoformate (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-0d1c6bb3405e44ea86a02dfee8548b2f
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07238812B2
Reaction notes
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