反应 #66097

反应方程式

Bis(2-chloroethyl)ether

sodium ethoxide

diethyl malonate

sodium ethoxide

sodium

→

tetrahydropyran-4,4-dicarboxylic acid diethyl ester

收率 44.0%

溶剂

ethanol

ethanol

ethanol

ethanol

反应条件

后处理

1. 1
   温度the mixture was heated
2. 2
   温度at reflux overnight
3. 3
   workup.ADDITIONwas added
4. 4
   温度The mixture was heated
5. 5
   温度at reflux for 48 h
6. 6
   温度then cooled
7. 7
   过滤filtered
8. 8
   其他to remove the precipitated sodium chloride
9. 9
   浓缩the filtrate was concentrated to dryness
10. 10
    workup.ADDITIONWater was added to the residue which
11. 11
    萃取was then extracted with ether (3×25 mL)
12. 12
    洗涤The combined ether layers were washed with water, brine
13. 13
    干燥dried over anhydrous sodium sulfate
14. 14
    浓缩Concentration under reduced pressure

实验过程

A solution of diethyl malonate (15.2 mL, 99.8 mmol) in ethanol (10 mL) was added dropwise to a solution of sodium ethoxide in ethanol [freshly prepared from sodium (2.3 g, 100 mmol) and ethanol (30 mL)] at ambient temperature and stirred for 10 min. Bis(2-chloroethyl)ether (12 mL, 102 mmol) was added dropwise then the mixture was heated at reflux overnight. It was then cooled to 10° C. before another portion of freshly-prepared sodium ethoxide in ethanol [prepared from sodium (2.3 g, 100 mmol) and ethanol (30 mL)] was added. The mixture was heated at reflux for 48 h then cooled, filtered to remove the precipitated sodium chloride then the filtrate was concentrated to dryness. Water was added to the residue which was then extracted with ether (3×25 mL). The combined ether layers were washed with water, brine and dried over anhydrous sodium sulfate. Concentration under reduced pressure yielded tetrahydropyran-4,4-dicarboxylic acid diethyl ester (10.1 g, 44%) as a mobile oil.

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