Methyl cyanoacetate → HCID 69190709, compound

Temperature

0 °C

Aqueous NaOH solution (1M, 20 mL) was added slowly to a solution of sodium hydrogensulphide hydrate (4.1 g, 73 mmol) in water (16 mL) at 0° C. The reaction mixture was degassed and flushed with nitrogen before the addition of 1-bromo-3,3,3-trifluoroacetone (10 g, 52 mmol). After stirring at 0° C. for 50 minutes, methyl cyanoacetate (3.8 mL, 54 mmol) was added, followed by triethylamine (7.6 mL, 54 mmol), and the reaction mixture was allowed to warm to room temperature. The reaction mixture was then diluted with EtOAc and separated. The aqueous layer was washed with EtOAc and the combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo to afford a brown solid. Recrystallisation from EtOAc/hexane gave the title compound (4.1 g) as a brown solid. LCMS (pH 10) RT 1.08 minutes; MS (m/z) 245 [M+H]+.

1. customThe reaction mixture was degassed
2. temperatureto warm to room temperature
3. customseparated
4. washThe aqueous layer was washed with EtOAc
5. washthe combined organic layers were washed with brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo
8. customto afford a brown solid
9. customRecrystallisation from EtOAc/hexane

ORD record

ord-33ea409d0f0543a889802d7cae37f6ad

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09227984B2