反応 #63993

反応方程式

diisopropylamine

hydrochloric acid

n-heptanoic acid

methyl iodide

n-butyl lithium

→

2-methylheptanoic acid

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他To a cold (0° C.) solution of 100 ml
2. 2
   温度The resulting solution was cooled to 0° C.
3. 3
   workup.STIRRINGThe reaction was stirred at room temperature under nitrogen for 1.5 hours
4. 4
   抽出extracted with diethyl ether (3×100 ml.)
5. 5
   洗浄washed with 10% hydrochloric acid, water, 20% sodium bisulfite
6. 6
   乾燥a brine solution and dried over magnesium sulfate
7. 7
   その他The solvent was removed in vacuo
8. 8
   workup.DISSOLUTION, dissolved in methanol containing 5.1 g
9. 9
   workup.STIRRINGAfter stirring overnight the mehtanol
10. 10
    その他was removed
11. 11
    workup.DISSOLUTIONthe residue dissolved in 150 ml
12. 12
    洗浄The aqueous layer was washed with ether (2×100 ml.)
13. 13
    抽出The product was extracted with ether
14. 14
    洗浄washed with a 20% sodium bisulfite solution and brine
15. 15
    乾燥dried over magnesium sulfate
16. 16
    その他Removal of the ether
17. 17
    その他gave 5.0 g

実験手順

To a cold (0° C.) solution of 100 ml. of dry tetrahydrofuran containing 11.8 ml. of dry diisopropylamine and 55 ml. of 1.6M n-butyl lithium was added 5.4 ml. of n-heptanoic acid and the mixture allow to stir at room temperature for one hour. The resulting solution was cooled to 0° C. and 7.2 ml. of methyl iodide was added. The reaction was stirred at room temperature under nitrogen for 1.5 hours, and was then poured into 10% hydrochloric acid and extracted with diethyl ether (3×100 ml.). The extracts were combined, washed with 10% hydrochloric acid, water, 20% sodium bisulfite and a brine solution and dried over magnesium sulfate. The solvent was removed in vacuo and the residue, 5.61 g., dissolved in methanol containing 5.1 g. of potassium hydroxide. After stirring overnight the mehtanol was removed and the residue dissolved in 150 ml. of water. The aqueous layer was washed with ether (2×100 ml.) and acidified with 10% hydrochloric acid. The product was extracted with ether, washed with a 20% sodium bisulfite solution and brine and dried over magnesium sulfate. Removal of the ether gave 5.0 g. of the product as a yellow liquid.

出典