反应 #5352

反应方程式

potassium carbonate

water

azelaic acid monomethyl ester

→

8-carbomethoxyoctan-1-ol

溶剂

tetrahydrofuran

diethyl ether

反应条件

后处理

1. 1
   workup.ADDITIONadded at such a rate as
2. 2
   其他the organic layer is separated
3. 3
   萃取The aqueous layer is extracted three times with diethyl ether
4. 4
   洗涤The combined extracts are washed with brine
5. 5
   干燥dried over Na2SO4
6. 6
   过滤filtered
7. 7
   浓缩concentrated in vacuo

实验过程

To a solution of 165 mL (165 mmol) of a 1.0M solution of boranetetrahydrofuran complex in tetrahydrofuran in 200 mL of dry diethyl ether at 0° C. is added dropwise 25.0 g (123 mmol) of azelaic acid monomethyl ester, added at such a rate as to prevent excessive release of gas and exothermicity. The solution is allowed to warm to room temperature overnight and is worked up by slowly adding water until gas evolution ceases. Then solid potassium carbonate is added and the organic layer is separated. The aqueous layer is extracted three times with diethyl ether. The combined extracts are washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to give 8-carbomethoxyoctan-1-ol as a colorless oil.

来源