반응 #312533

반응 방정식

methanol

4-bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one

2,6-lutidine

MeOH

→

4-methoxy-2-(6-carboxyhexyl)cyclopent-2-en-1-one

반응 조건

후처리

1. 1
   workup.ADDITIONthe mixture is treated with 2.66 g
2. 2
   workup.STIRRINGis stirred at ambient temperature for 45 minutes
3. 3
   기타Silver bromide is removed by filtration
4. 4
   농축the filtrate is concentrated to a volume of 40 ml
5. 5
   workup.ADDITIONThe solution is treated with saturated sodium chloride solution
6. 6
   추출extracted with ether
7. 7
   세척The extract is washed successively with 0.5 N hydrochloric acid solution, water, and saturated sodium chloride solution
8. 8
   건조dried over magnesium sulfate
9. 9
   농축and concentrated
10. 10
    기타Partition chromatography of the residue on Celite
11. 11
    기타gives an oil, λmax

실험 절차

To a stirred solution of 5.30 g. of crude 4-bromo-2-(6-carboxyhexyl)cyclopent-2-en-1-one (Example 8) in 85ml. of methanol at 0°-3° C. is added 4.40 g. (22.6 mmole) of silver fluoborate in one portion. After 2 minutes, the mixture is treated with 2.66 g. (24.8 l mmoles) of 2,6-lutidine. After stirring for 30 minutes at 0°-3° C. the mixture is stirred at ambient temperature for 45 minutes. Silver bromide is removed by filtration, and the filtrate is concentrated to a volume of 40 ml. The solution is treated with saturated sodium chloride solution and extracted with ether. The extract is washed successively with 0.5 N hydrochloric acid solution, water, and saturated sodium chloride solution; dried over magnesium sulfate; and concentrated. Partition chromatography of the residue on Celite gives an oil, λmax.MeOH =220 mμ (7450); νmax.=1715 (carbonyl groups) and 1095 cm-1 (methoxy group).

출처