反応 #2267077

反応方程式

H3PO2

15

6-Amino-3-methyl-1-(4-nitrophenyl)-7-methoxyisochroman

NaNO2

→

desired product 16

収率 86.0%

3-Methyl-1-(4-nitrophenyl)-7-methoxyisochroman

収率 86.0%

溶媒

H2SO4

反応条件

後処理

1. 1
   温度After refluxing for 5 hours
2. 2
   抽出the solution was extracted with ethyl acetate three times
3. 3
   乾燥The combined organic phases were dried over Na2SO4
4. 4
   その他Removal of the solvent
5. 5
   その他afforded the crude product
6. 6
   その他Purification of the crude product

実験手順

Solution of 15 (100 mg, 0.32 mmol) in 5 ml of 4N H2SO4 was treated with NaNO2 (29.6 mg, 1.16 eq) at 0° C. for 15 min, followed by adding H3PO2 (50%, 0.25 ml) at such temperature. After refluxing for 5 hours, the solution was extracted with ethyl acetate three times. The combined organic phases were dried over Na2SO4. Removal of the solvent afforded the crude product. Purification of the crude product by using silica gel column gave the desired product 16 (82 mg, 86%).

出典