Sulfuric Acid → 4-(1-trans-Tridecenyl)pyrrole-2-carboxylic acid

反応式

[OH-].[Na+].[CH:3](/[C:16]1[CH:17]=[C:18]([C:21]([O:23]C)=[O:22])[NH:19][CH:20]=1)=[CH:4]\[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].S(=O)(=O)(O)O>C(O)C>[CH:3](/[C:16]1[CH:17]=[C:18]([C:21]([OH:23])=[O:22])[NH:19][CH:20]=1)=[CH:4]\[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

参加物

実験手順

An aqueous solution (8 ml) containing 340 mg (8.0 mmol) of 95% sodium hydroxide was added to an ethanol solution (20 ml) of 1.30 g (4.3 mmol) of methyl 4-(1-trans-tridecenyl)pyrrole-2-carboxylate prepared in Example 48, and the whole was heated under reflux for 1 hour. The reaction mixture was acidified with 6N sulfuric acid and extracted with ethyl acetate. The extract was washed with an aqueous saturated solution of sodium chloride, dried over anhydrous magnesium sulfate and treated with activated carbon. After removing the solvent under reduced pressure, the resulting residue was recrystallized from a mixed solution of hexane and tetrahydrofuran to give 940 mg (72% yield) of 4-(1-trans-tridecenyl)pyrrole-2-carboxylic acid, m.p. 161°-163° C.