Potassium Carbonate → HCID 178450943, compound

To a round-bottomed flask (100 ml) under an argon atmosphere was added tert-butyl 2-[(E)-(4-chlorophenyl)methyleneamino]propanoate (CAN 208927-33-7, 1.6 g, 5.97 mmole), 1-bromomethyl cyclopropane (CAN 7051-34-5, 4.5 ml, 51.43 mmole), and tetrabutyl ammonium chloride (0.166 g, 0.6 mmole). A mixture of potassium hydroxide (1.67 g, 29.85 mmole)/potassium carbonate (4.12 g, 29.85 mmole) was finely grained using a mortar and was added to the reaction mixture. The resulting mixture was stirred vigorously at room temperature for 24 h. Dichloromethane was added and the reaction mixture was filtered to remove insolubles. The solids were washed twice with 40 ml dichloromethane and the filtrate was evaporated to dryness on a rotary evaporator. The residue was taken up in ether (80 ml) and the organic solution was washed twice with 80 ml water. The organic phase was dried over sodium sulfate and evaporated in vacuo to yield the title compound (2.08 g) as a crude yellow oil which was used without any purification; MS (ESI, m/z): 322.3 (M+H+).

1. additionwas added to the reaction mixture
2. filtrationthe reaction mixture was filtered
3. customto remove insolubles
4. washThe solids were washed twice with 40 ml dichloromethane
5. customthe filtrate was evaporated to dryness on a rotary evaporator
6. washthe organic solution was washed twice with 80 ml water
7. dry with materialThe organic phase was dried over sodium sulfate
8. customevaporated in vacuo

ORD record

ord-fc12e85e545940a08be5aea1b810d71e

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409866B2