반응 #577219

반응 방정식

3-Bromo-1-propene

7-hydroxy-4-methylcoumarin

potassium carbonate

→

2

수율 96.2%

7-Allyloxy-4-methylcoumarin

수율 96.2%

용매

acetone

반응 조건

후처리

1. 1
   온도The resulting mixture was then refluxed for 4 h
2. 2
   온도to cool
3. 3
   여과the K2CO3 filtered off
4. 4
   세척washed with fresh acetone
5. 5
   기타The solvent was removed in vacuo
6. 6
   기타the residue was crystallized from methanol

실험 절차

3-Bromo-1-propene (2.95 mL, 34.06 mmol) was added dropwise under argon to a stirred mixture of 7-hydroxy-4-methylcoumarin 1 (2.0 g, 11.35 mmol) and anhydrous potassium carbonate (K2CO3) (2.35 g, 17.03 mmol) in acetone (50 mL). The resulting mixture was then refluxed for 4 h, after which it was allowed to cool, and the K2CO3 filtered off and washed with fresh acetone. The solvent was removed in vacuo and the residue was crystallized from methanol to afford 2 as white-cream crystals (2.36 g, 96%). TLC (hexane/ethyl acetate, 1:3): Rf=0.63. mp 110° C. 1H NMR (CDCl3, 500 MHz) δ 2.39 (s, 3H, CH3), 4.60 (d, J=5.0 Hz, 2H, CH2), 5.33 (d, J=10.5 Hz, 1H), 5.44 (d, J=17.5 Hz, 1H), 6.05 (m, 1H), 6.12 (s, 1H), 6.80 (s, 1H), 6.87 (dd, J=1.5, 9.0 Hz, 1H), 7.49 (d, J=9.0 Hz, 1H). 13C NMR (CDCl3, 125 MHz) δ 18.70, 69.29, 101.84, 112.05, 112.79, 113.75, 118.51, 125.64, 132.31, 152.61, 152.26, 161.26, 161.65. ESIMS calcd for C13H13O3 [M+H]+ 217.1, found 217.1.

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