Reaktion #55588

Reaktionsgleichung

lithium hydride

methyllithium

oct-7-enoic acid

→

title compound

Non-8-en-2-one

Lösungsmittel

ether

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature
2. 2
   SonstigeThis mixture was quenched
3. 3
   workup.ADDITIONby pouring the slurry into rapidly stirred 10% aqueous hydrochloric acid (1.2 liter) and wet ice
4. 4
   ExtraktionThe resulting mixture was extracted with ether (3×700 ml)
5. 5
   WaschenThe continued ether extracts were washed with 10% aqueous sodium hydroxide
6. 6
   Trocknenwith saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate
7. 7
   SonstigeThe solvent was removed in vacuo

Vorschrift

To a stirred mixture of 11.0 g lithium hydride in 800 ml of anhydrous ether, there was added dropwise 164 g of oct-7-enoic acid (prepared in Example 22 B-2) in 800 ml of anhydrous ether and the mixture was cooled to 0° C. and 650 ml of 2 M methyllithium in ether was added dropwise and then allowed to warm to room temperature and stir for 4.5 hr. This mixture was quenched by pouring the slurry into rapidly stirred 10% aqueous hydrochloric acid (1.2 liter) and wet ice. The resulting mixture was extracted with ether (3×700 ml). The continued ether extracts were washed with 10% aqueous sodium hydroxide and then with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to yield 118.9 g of the title compound having the following physical characteristics:

Quelle