反应 #51203

反应方程式

EtOAc

2,3-Dihydrobenzo[b]furan

SnCl4

Dichloromethyl methyl ether

→

title product

收率 0.6%

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

收率 0.6%

溶剂

pentane

DCM

反应条件

后处理

1. 1
   其他to produce a pale yellow solution
2. 2
   workup.STIRRINGthe solution stirred for 30 min
3. 3
   其他after which time the cooling bath was removed
4. 4
   workup.ADDITIONthe reaction poured onto ice-water (1000 ml)
5. 5
   其他The organic layer was separated
6. 6
   洗涤washed 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
   过滤Filtration
9. 9
   其他through Celite and evaporation
10. 10
    其他gave a black oil, which

实验过程

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%.

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