Reaction #577220

Reaction equation

7-Allyloxy-4-methylcoumarin

N,N-diethylaniline

→

3

Yield 88.0%

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

Yield 88.0%

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was then cooled, during which some of the product
2. 2
   Otherprecipitated
3. 3
   workup.ADDITIONHexane (10 mL) was added in order
4. 4
   Otherto precipitate out the remaining product
5. 5
   FiltrationThe precipitate was filtered
6. 6
   Washwashed with hexane
7. 7
   Otherdried under vacuum

Procedure

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.

Source