苯酚锂盐和1,4-二溴-2-丁烯在加热条件下反应得到苯并二氢呋喃的反应。

反应机理

反应实例

2-Vinyl-2,3-dihydrobenzofuran (3). n-Butyllithium (6.25 mL of 1.6 M hexane solution) was added to a solution of phenol (0.94 g, 10 mmol) in anh PhMe (40 mL) under N2 and the mixture was stirred

for 15 min at r.t. 1,4-Dibromo-2-butene 2 (2.14 g, 10 mmol) in PhMe (10 mL) was added and the resulting slurry was heated under reflux for 22 h. The reaction mixture was cooled to r.t. and subjected

to usual workup and chromatography on silica gel using hexane to give 3 (0.70 g, 48%) as an oil, bp 115 ℃/20 torr.

【Casiraghi G, Tetrahedron, 1983, 39, 169】

【Bulletin of the Chemical Society of Japan, 2007, 80, 578-582】

相关文献

1 Nickl J Chem Ber 1958 91 553

2 Casiraghi G Angew Chem Int 1978 17 684

3 Casiraghi G J Org Chem 1979 44 803

4 Kawase Y Chem Lett 1979 7 253

5 Casiraghi G Tetrahedron 1983 39 169

6 Choi HD Arch Pharm Res 2004 27 19

7 Li JH Synthesis 2008 3988

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 342-343.