ChemicalBook CAS DataBase List Diethyl allylmalonate

Diethyl allylmalonate synthesis

11synthesis methods

Product Name:Diethyl allylmalonate
CAS Number:2049-80-1
Molecular formula:C10H16O4
Molecular Weight:200.23

Diethyl allyl malonate is obtained by reacting diethyl malonate with allyl bromide.
Under nitrogen atmosphere, to a 500 mL three-neck round bottom flask was added diethyl malonate (20 g), anhydrous potassium carbonate (43 g) and anhydrous CH3CN (200 mL). The reaction mixture was stirred at room temperature for 10 minutes, then allyl bromide (23 g) was slowly added to the reaction mixture at room temperature. The reaction mixture was heated to 80°C for 24 hours. The reaction mixture was cooled to room temperature and filtered through a bed of celite. The celite bed was washed with acetonitrile (100 mL) and the combined filtrates were concentrated to give diethyl allylmalonate (24 g) as a colorless liquid.

591-87-7 Synthesis

591-87-7
188 suppliers
$10.00/10g

105-53-3
751 suppliers
$5.00/25g

2049-80-1
183 suppliers
$33.70/25g

3195-24-2
108 suppliers
$7.07/1gm:

Yield:2049-80-1 91% ，3195-24-2 8%

Reaction Conditions:

with C₃₃H₃₃N₂O₄PPd;potassium carbonate in N,N-dimethyl-formamide at 20; for 15 h;Schlenk technique;Inert atmosphere;Tsuji-Trost Allylation;Reagent/catalyst;

Steps:

A Schlenk tube equipped with a magnetic stirring bar and a rubber septum was charged with diethyl malonate 4 (80 mg,0.5 mmol) and DMF (1 mL). The mixture was evacuated/refilled three times with argon. Then complex 1, 2 or 3 (0.01 mmol) was added and the mixture was stirred for 5 min. Allyl acetate (125 mg, 1.25 mmol, ~0.15 mL) was added. After 10 min stirring, freshly powdered K2CO3 (207 mg, 1.5 mmol) was added. After each opening, the flack was evacuated and refilled with argon. The mixture was stirred at ~20 C for 15 h. The aliquot of the reaction mixture was treated with water, extracted with diethyl ether, and analyzed by GC.

References:

Peganova;Kalsin;Ustynyuk;Vasil'Ev [Russian Chemical Bulletin,2014,vol. 63,# 10,p. 2305 - 2308]

106-95-6 Synthesis