Diethyl isopropylmalonate synthesis
- Product Name:Diethyl isopropylmalonate
- CAS Number:759-36-4
- Molecular formula:C10H18O4
- Molecular Weight:202.25
Yield:759-36-4 97%
Reaction Conditions:
Stage #1:diethyl malonate with sodium ethanolate
Stage #2:isopropyl bromide for 10.5 - 10.75 h;Heating / reflux;
Stage #3: with water;ammonium chlorideProduct distribution / selectivity;
Steps:
1.1
Example 1; Step 1:; To a stirred solution of 21 wt. % sodium ethoxide (245 mL, 0.6 M), was added diethyl malonate (80 mL, 0.5 M). Immediately, a white precipitate formed. The mixture was then heated to reflux (the white precipitate dissolved during this process) and 2-bromopropane (70 mL, 0.75 M) was added dropwise during 30-45 min. Refluxing was continued for over 10 hr. After cooling to room temperature, the mixture was evaporated in vacuo. The residue was dissolved in ether, washed with saturated NH4Cl solution, dried with MgSO4, filtered, and evaporated in vacuo to give 98 g (97%) of diethyl isopropyl malonate (1) as a pale brown oil. The crude product was used directly in the next reaction.1H NMR (200 MHz, CDCl3) δ 0.98 (6H, d, J=6.6 Hz), 1.25 (6H, t, J=7.2 Hz), 2.32-2.43 (1H, m), 3.09 (1H, d, J=8.6 Hz), 4.17 (4H, q, J=7.2 Hz).
References:
Gilead Sciences, Inc.;Korea Research Institute of Chemical Technology US2009/163712, 2009, A1 Location in patent:Page/Page column 13-14
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