Dimethyl butylmalonate synthesis
- Product Name:Dimethyl butylmalonate
- CAS Number:39520-22-4
- Molecular formula:C9H16O4
- Molecular Weight:188.22
Yield:39520-22-4 75%
Reaction Conditions:
Stage #1: malonic acid dimethyl esterwith sodium hydride in N,N-dimethyl-formamide;mineral oil; for 0.25 h;Inert atmosphere;
Stage #2: 1-iodo-butane in N,N-dimethyl-formamide;mineral oil at 0 - 25; for 2 h;Inert atmosphere;
Steps:
General procedure 1 (GP1)
General procedure: alkylation: A RBF equipped with a stirring bar was charged with NaH 60% (1.0 equiv) and purged withargon. DMF (V mL) was added and the RBF was cooled to 0 °C (ice/water bath). Malonate 1 (1.1 equiv) was added dropwise with asyringe and the mixture was stirred for 15 min. The alkyl halide 2 (1.0 equiv) was then added dropwise with a syringe. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. Then, the resulting mixture was poured in sat aq NH4Cl (3 V)and the resulting solution was extracted with Et2O (3 × 2 V). The combined organic layers were washed with water (10 V) and brine (5V), dried (Na2SO4), and evaporated. Purification by FC afforded the expected product 3.
References:
Condon, Sylvie;Le Gall, Erwan;Pichon, Christophe;Presset, Marc;Xavier, Tania [Beilstein Journal of Organic Chemistry,2021,vol. 17,p. 2085 - 2094] Location in patent:supporting information
