Chlorotrimethylsilane → HCID 53876422, compound

Temperature

-30 °C

In 15 ml of acetonitrile was dissolved 795 mg of methyl 2-methoxyimino-3-oxobutyrate, followed by addition of 2.1 ml of triethylamine. Then, 1.9 ml of chlorotrimethylsilane was added dropwise with ice-cooling and the mixture was stirred at 20°-25° C. for 1 hour for silylation. The reaction mixture was concentrated under reduced pressure and the residue was suspended in 15 ml of tetrahydrofuran. The suspension was filtered in a nitrogen gas stream to remove insolubles. The filtrate was cooled to -30° C. and 0.405 ml of sulfuryl chloride was added dropwise. After the temperature of the system was increased to 20° C., the mixture was concentrated under reduced pressure. The concentrate was chromatographed on a silica gel column and elution was carried out with 100 ml of hexane-ether (1:1, v/v). The eluate was concentrated under reduced pressure to give 813 mg of methyl 4-chloro-2-methoxyimino-3-oxobutyrate as colorless oil. Yield 84.1%.

1. temperaturecooling
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. filtrationThe suspension was filtered in a nitrogen gas stream
4. customto remove insolubles
5. addition0.405 ml of sulfuryl chloride was added dropwise
6. temperatureAfter the temperature of the system was increased to 20° C.
7. concentrationthe mixture was concentrated under reduced pressure
8. customThe concentrate was chromatographed on a silica gel column and elution
9. concentrationThe eluate was concentrated under reduced pressure

ORD record

ord-b596f37403494467875489c317fba76c

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04845257