Diethyl ethylmalonate → HCID 178437345, compound

To a stirred solution of sodium ethoxide (21% in ethanol, 349 mL, 1.06 mol) in dry ethanol (500 mL) was added formamidine acetate (30.4 g, 0.29 mol) in lots at 0° C. under nitrogen. The reaction mixture was stirred at this temperature for 15 min and then added a solution of diethyl-ethylmalonate (50.0 g, 0.26 mol) in ethanol (200 mL) in drops at 0° C. under nitrogen. The reaction mixture was stirred at RT for 14 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude residue was dissolved in water (250 mL) and acidified (pH ˜3 to 4) with aqueous solution HCl (1.5 N, 100 mL). The resulting solid was filtered off, washed with water (100 mL) and dried under vacuum to afford the titled compound (27.0 g, 72.5%) as white solid. LCMS: Mass found (M+, 141.0), 1H NMR (400 MHz, DMSO-d6) 11.54 (bs, 2H), 7.86 (s, 1H), 2.28-2.22 (m, 2H), 0.95-0.91 (m, 3H).

1. stirringThe reaction mixture was stirred at RT for 14 h
2. customAfter completion of the reaction
3. concentrationthe reaction mixture was concentrated under reduced pressure
4. dissolutionThe crude residue was dissolved in water (250 mL)
5. filtrationThe resulting solid was filtered off
6. washwashed with water (100 mL)
7. customdried under vacuum

ORD record

ord-9027825e27534aa8b13765b4e6d41bb6

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09145392B2