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7-Allyloxy-4-methylcoumarin

N,N-diethylaniline

→

3

수율 88.0%

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

수율 88.0%

반응 조건

후처리

1. 1
   온도The reaction mixture was then cooled, during which some of the product
2. 2
   기타precipitated
3. 3
   workup.ADDITIONHexane (10 mL) was added in order
4. 4
   기타to precipitate out the remaining product
5. 5
   여과The precipitate was filtered
6. 6
   세척washed with hexane
7. 7
   기타dried under vacuum

실험 절차

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.

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