Piperonyl alcohol → 5-Methyl-4-nitro-thiophene-2-carboxylic acid 1,3-benzodioxol-5-ylmethyl ester

Reaction equation

C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][C:14]1[S:18][C:17]([C:19]([OH:21])=[O:20])=[CH:16][C:15]=1[N+:22]([O-:24])=[O:23].[CH2:25](O)[C:26]1[CH:34]=[CH:33][C:32]2[O:31][CH2:30][O:29][C:28]=2[CH:27]=1>>[O:31]1[C:32]2[CH:33]=[CH:34][C:26]([CH2:25][O:20][C:19]([C:17]3[S:18][C:14]([CH3:13])=[C:15]([N+:22]([O-:24])=[O:23])[CH:16]=3)=[O:21])=[CH:27][C:28]=2[O:29][CH2:30]1

Participants

Reactant 3

HCID 10322Piperonyl alcohol

HCID 682631,1'-Carbonyldiimidazole

HCID 31107845-Methyl-4-nitrothiophene-2-carboxylic acid

Product 1

HCID 696928385-Methyl-4-nitro-thiophene-2-carboxylic acid 1,3-benzodioxol-5-ylmethyl esterYield 77.8%

Procedure

The title compound was prepared according to the procedure described for Example 2 using carbonyldiimidazole (0.75 g, 4.3 mmol), 5-methyl-4-nitro-thiophene-2-carboxylic acid (0.6 g, 3.2 mmol), and piperonyl alcohol (0.5 g, 3.3 mmol) to afford 0.8 g of 5-methyl-4-nitro-thiophene-2-carboxylic acid 1,3-benzodioxol-5-ylmethyl ester. A sample of the product was triturated in ethanol, cooled, filtered, and dried to give product with a mp 78-79° C.