تفاعل #4768

معادلة التفاعل

lithium aluminum hydride

methyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate

diethyl ether

lithium aluminum hydride

→

5-hydroxymethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine

المردود 72.5%

المذيبات

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةunder cooling at -50°~-40° C
2. 2
   غسيلThe separated organic layer was washed with 15% sulfuric acid (400 ml)
3. 3
   استخلاصextracted with ethyl acetate (1 l)
4. 4
   غسيلThe organic layer was washed with saturated aqueous sodium bicarbonate and aqueous sodium chloride successively
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىThe residue was recrystallized from diethyl ether

الإجراء التجريبي

To a suspension of lithium aluminum hydride (12.24 g) in a mixture of dry tetrahydrofuran (180 ml) and diethyl ether (360 ml) was dropwise added a solution of methyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (45 g) in dry tetrahydrofuran (180 ml) under cooling at -50°~-40° C. The excess lithium aluminum hydride was decomposed by a careful addition to ice water. The separated organic layer was washed with 15% sulfuric acid (400 ml) and extracted with ethyl acetate (1 l). The organic layer was washed with saturated aqueous sodium bicarbonate and aqueous sodium chloride successively and concentrated in vacuo. The residue was recrystallized from diethyl ether to give 5-hydroxymethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine (30 g).

المصدر