تفاعل #5352

معادلة التفاعل

potassium carbonate

water

azelaic acid monomethyl ester

→

8-carbomethoxyoctan-1-ol

المذيبات

tetrahydrofuran

diethyl ether

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONadded at such a rate as
2. 2
   أخرىthe organic layer is separated
3. 3
   استخلاصThe aqueous layer is extracted three times with diethyl ether
4. 4
   غسيلThe combined extracts are washed with brine
5. 5
   تجفيفdried over Na2SO4
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated in vacuo

الإجراء التجريبي

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.

المصدر