Reaction #63993

Reaction equation

diisopropylamine

hydrochloric acid

n-heptanoic acid

methyl iodide

n-butyl lithium

→

2-methylheptanoic acid

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   OtherTo a cold (0° C.) solution of 100 ml
2. 2
   TemperatureThe 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
   Extractionextracted with diethyl ether (3×100 ml.)
5. 5
   Washwashed with 10% hydrochloric acid, water, 20% sodium bisulfite
6. 6
   Dryinga brine solution and dried over magnesium sulfate
7. 7
   OtherThe 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
    Otherwas removed
11. 11
    workup.DISSOLUTIONthe residue dissolved in 150 ml
12. 12
    WashThe aqueous layer was washed with ether (2×100 ml.)
13. 13
    ExtractionThe product was extracted with ether
14. 14
    Washwashed with a 20% sodium bisulfite solution and brine
15. 15
    Dryingdried over magnesium sulfate
16. 16
    OtherRemoval of the ether
17. 17
    Othergave 5.0 g

Procedure

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.

Source