ChemicalBook CAS DataBase List VINYL LITHIUM

VINYL LITHIUM synthesis

11synthesis methods

Product Name:VINYL LITHIUM
CAS Number:917-57-7
Molecular formula:C2H3Li
Molecular Weight:33.99

Vinyllithium is prepared by a variety of methods. Direct metalation of Ethylene with Lithium metal in dimethoxymethane yields vinyllithium contaminated with lithium hydride, and other organolithio species, such as butyllithium and 1,4-dilithiobutane. Direct formation from ethylene can also be accomplished using Potassium t-Butoxide, n-Butyllithium, and TMEDA (N,N,N′,N′-Tetramethylethylenediamine) in hexane at -40 °C, followed by treatment of the vinylpotassium with Lithium Bromide. The lithium-halogen exchange reaction has been used, starting from vinyl chloride and lithium/sodium dispersions, or from vinyl bromide with 2 equiv of t-Butyllithium in either a Trapp solvent mixture at - 120 °C or ether at -78 °C. This is the most convenient procedure, but lithium halide is formed during the reaction and is present as a contaminant. Halide-free vinyllithium can be prepared by transmetalation of Tetravinylstannane with phenyl- or butyllithium, of tetravinyllead with either lithium metal or Phenyllithium, or of divinylmercury with lithium dispersion in pentane.

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917-54-4
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Yield:-

Reaction Conditions:

in diethyl ether at 0; for 0.5 h;Inert atmosphere;

Steps:

1-Phenylmethyl2-methyl6- (tert-butyldiphenylsilyloxymethyl) -3-vinylpiperidine-1,2- dicarboxylate (13)
A stirred solution of tetravinyltin (4 mL, 24.5 mmol) in Et2O (10 mL)was treated with a solution of MeLi (0.98 M in Et2O, 100 mL, 98 mmol)at 0 °C, and the reaction mixture was stirred at 0 °C for 30 min. Astirred suspension of CuI (9.33 g, 49.0 mmol) in Et2O (20 mL) wastreated with a solution of vinyllithium (prepared as above) at -78 °C,and the resulting mixture was stirred at ~-78 to -35°C for 30 min. Asolution of 4 (6.1 g, 11.2 mmol) in Et2O (20 mL) was added dropwise tothe reaction mixture via a double-tipped stainless steel needle at -78°C. The reaction mixture was stirred at ~-78 to -10 °C for 1 h, and thenthe reaction was quenched with saturated aqueous NH4Cl. The aqueousmixture was diluted with CH2Cl2, and the insoluble material wasfiltered off. The organic layer was separated and the aqueous layer wasextracted with CH2Cl2 (2 × 30 mL). The organic layer and extractswere combined, dried and evaporated to give a pale yellow oil, whichwas chromatographed on silica gel (100 g, hexane:acetone =~25:1-20:1) to afford compound 13 as: Pale yellow oil;

References:

Zhou, De-Jun;Wang, Zhen-Hui;Zhang, Yan-Ru;Cui, Zheng-Guo [Journal of Chemical Research,2017,vol. 41,# 2,p. 98 - 105]

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References