反応 #77318

反応方程式

Diethyl malonate

sodium ethoxide

2-Bromoethyl ether

→

title compound

収率 61.3%

Diethyl Tetrahydropyran-4,4-dicarboxylate

収率 61.3%

溶媒

ethanol

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred
2. 2
   温度at reflux for 3 h
3. 3
   温度The mixture was then cooled
4. 4
   その他evaporated in vacuo
5. 5
   その他the residue partitioned between water and dichloromethane
6. 6
   その他The organic layer was separated
7. 7
   洗浄washed with water and brine
8. 8
   乾燥dried (MgSO4)
9. 9
   その他evaporated
10. 10
    その他The residue was then purified by flash column chromatography on silica gel
11. 11
    洗浄eluting with 4:1 hexanes/ether

実験手順

Diethyl malonate (32.0 g) was added to a solution of sodium ethoxide (1 equivalent) in ethanol and the solution was stirred for 30 min. 2-Bromoethyl ether (46.0 g) was then added and the mixture was stirred at reflux for 3 h. The mixture was then cooled, evaporated in vacuo and the residue partitioned between water and dichloromethane. The organic layer was separated and washed with water and brine, then dried (MgSO4) and evaporated. The residue was then purified by flash column chromatography on silica gel, eluting with 4:1 hexanes/ether, to give the title compound (28.0 g) as colourless liquid.

出典