Synthesis of ethyllithium

Preparation of ethyllithium (EtLi · LiBr)

Preparation of ethyllithium

Preparation of ethyllithium

18 g (2.57 mol) lithium containing 1-3 % of sodium are flattened with a hammer to 1.5 mm thickness and subsequently cut into the flask (chips of 2 x 10 x 1.5 mm) containing 800 ml DRY diethyl ether. The ether is cooled to – 25° and the air purged with dry nitrogen or argon (2 l/min during 1-2 min). In the dropping funnel 119.8 g, (1.1 mol), of ethyl bromide are placed and 10 g are added in one portion. After a few minutes a turbidity appears and a distinct rise of the temperature occurs. When, after about 10 min, the reaction has subsided, the remainder of the ethyl bromide is added slowly dropwise over 1 hour period, while keeping the temperature of the mixture between -15 and -20°C. The black coating disappears almost entirely from the lithium metal which has a bright silver-like color. After the addition is complete, stirring is continued at -15°C for an additional hour. The temperature is then allowed to rise to 0° and the glow on the metal gradually disappears. The obtained solution is ten poured into the storage flask, which previously has been filled with inert gas (it is not necessary to filter off the lithium chips). During filtration under inert atmosphere a fast stream (2 to 3 l/min) nitrogen or argon is passed through the reaction flask to protect the solution against attack by oxygen as shown in the picture bellow. Diethyl ether is added to bring the solution to a volume of 1 litre. After gentle shaking or swirling (homogenization), the titer is  determined: this is usually close to 1 molar corresponding to a yield of 90 %.

Preparative Polar Organometallic Chemistry; Vol 1; by L. Brandsma, H. D. Verkruijsse; Springer-Verlag Berlin Heidelberg; 17-18; 1987

IUPAC Name

lithium;ethane

InChI

InChI=1S/C2H5.Li/c1-2;/h1H2,2H3;/q-1;+1

InChI Key

QBZXOWQOWPHHRA-UHFFFAOYSA-N

Canonical SMILES

[Li+].C[CH2-]

Depositor-Supplied Synonyms

Ethyllithium, Ethyl lithium, Lithium, ethyl-, Ethyllithium solution, 811-49-4, ethyl-lithium, lithium ethane, lithium ethanide, LiEt, AC1L2WOA, 561452_ALDRICH, CHEBI:51468, CTK3E8392, BLHLJVCOVBYQQS-UHFFFAOYSA-N, LITHIUM(1+) ION ETHANIDE, EINECS 212-370-2, ANW-37419, AR-1J3240, AKOS015902627, RTR-025550, OR034672, OR344167, SC-69937, TR-025550, FT-0689289, I14-19816, Ethyllithium, typ. 8 % solution in Dibutyl Ether (typ. 1.7 M)

Removed Synonyms

CID79107, CID6093487, 85610-13-5

Share This

Leave a Reply

Your email address will not be published. Required fields are marked *