반응 #47110

반응 방정식

4-chromanol

dichloromethane

ethyl diazoacetate

→

product 475

[(1-Benzopyran-4-yloxy)methyl]acetic acid ethyl ester

용매

heptane

반응 조건

후처리

1. 1
   여과filtered through Celite
2. 2
   기타the filtrate is evaporated
3. 3
   기타the residue purified by chromatography on silica gel
4. 4
   세척elution with EtOAc:dichloromethane:hexane (10:20:70)

실험 절차

To a solution of 4-chromanol (1.5 g, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (0.95 mL, 9.0 mmol). The reaction mixture is stirred at rt for 30 min. The reaction mixture is diluted with heptane, filtered through Celite, and the filtrate is evaporated and the residue purified by chromatography on silica gel; elution with EtOAc:dichloromethane:hexane (10:20:70) gives 1.81 g of the product 475. 1H NMR (CDCl3) δ 7.35 (dd, 1H), 7.22 (dt, 1H), 6.90 (t, 1H), 6.84 (d, 1H), 4.56 (m, 1H), 4.36 (dd, 1H), 4.29 (dd, 1H), 4.23 (q, 2H), 4.19 (s, 2H), 2.18 (m, 1H), 2.05 (m, 1H), 1.30 (t, 3H); MS: m/z 236 (M++1).

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