反应 #577220

反应方程式

7-Allyloxy-4-methylcoumarin

N,N-diethylaniline

→

3

收率 88.0%

8-Allyl-7-hydroxyl-4-methyl-2H-chromen-2-one

收率 88.0%

反应条件

后处理

1. 1
   温度The reaction mixture was then cooled, during which some of the product
2. 2
   其他precipitated
3. 3
   workup.ADDITIONHexane (10 mL) was added in order
4. 4
   其他to precipitate out the remaining product
5. 5
   过滤The precipitate was filtered
6. 6
   洗涤washed with hexane
7. 7
   其他dried under vacuum

实验过程

7-Allyloxy-4-methylcoumarin 2 (1.0 g, 4.62 mmol) was dissolved in N,N-diethylaniline (8 mL) in a sealed vial and heated to 250° C. for 25 min under microwave. The reaction mixture was then cooled, during which some of the product precipitated. Hexane (10 mL) was added in order to precipitate out the remaining product. The precipitate was filtered, washed with hexane, and dried under vacuum to yield 3 as a pale-yellow solid (0.88 g, 88%). TLC (hexane/ethyl acetate, 1:3): Rf=0.5. mp 204° C. 1H NMR (CDCl3/CD3OD, 500 MHz) δ 2.43 (s, 3H, CH3), 3.57 (d, J=6.0 Hz, 2H, CH2), 4.95 (d, J=10.0 Hz, 1H), 5.04 (d, J=17.0 Hz, 1H), 5.97 (m, 1H), 6.10 (s, 1H), 6.86 (d, J=9.0 Hz, 1H), 7.46 (d, J=9.0 Hz, 1H). 13C NMR (CDCl3/CD3OD, 125 MHz) δ 18.85, 27.66, 110.78, 113.20, 113.73, 114.93, 115.41, 124.38, 136.16, 153.89, 155.88, 160.18, 163.92. ESIMS calcd for C13H13O3 [M+H]+ 217.1. Found 217.2.

来源