반응 #518966

반응 방정식

EtOAc

2,3-Dihydrobenzo[b]furan

SnCl4

Dichloromethyl methyl ether

→

title product

수율 0.6%

2,3-Dihydrobenzo[b]furan-7-carboxaldehyde

수율 0.6%

용매

pentane

DCM

반응 조건

후처리

1. 1
   기타to produce a pale yellow solution
2. 2
   workup.STIRRINGthe solution stirred for 30 min
3. 3
   기타after which time the cooling bath was removed
4. 4
   workup.ADDITIONthe reaction poured onto ice-water (1000 ml)
5. 5
   기타The organic layer was separated
6. 6
   세척washed with water (2×100 ml), 2N HCl (100 ml) and brine (50 ml)
7. 7
   workup.ADDITIONcharcoal (30 g) and Na2SO4 were added to the solution
8. 8
   여과Filtration
9. 9
   기타through Celite and evaporation
10. 10
    기타gave a black oil, which

실험 절차

2,3-Dihydrobenzo[b]furan (Maybridge Chemicals) (25 g, 0.21 mole) was taken up in DCM (500 ml) and stirred under nitrogen at 0° C. SnCl4 (36.5 ml, 0.3 mole) was added in one portion to produce a pale yellow solution. Dichloromethyl methyl ether (18.8 ml, 0.21 mole) was then added and the solution stirred for 30 min, after which time the cooling bath was removed and the reaction poured onto ice-water (1000 ml). The organic layer was separated, washed with water (2×100 ml), 2N HCl (100 ml) and brine (50 ml), and then charcoal (30 g) and Na2SO4 were added to the solution. Filtration through Celite and evaporation gave a black oil, which was subjected to flash chromatography using 7-10% EtOAc in pentane to give the title product (190 mg, 0.01%); 1HNMR (400 MHz, CDCl3) δ: 3.24 (t, 2H), 4.75 (t, 2H), 6.93 (t, 1H), 7.40 (d, 1H), 7.59 (d, 1H), 10.2 (s, 1H); LRMS: (M+H) 149, TS+. Anal. Found: C, 72.98; H, 5.46%. C9H8O2 requires C, 72.96; H, 5.44%.

출처