Acetic Acid → HCID 14667723, compound

Temperature

0 °C

N-Benzyl-1-methoxy-N-[(trimethylsilyl)methyl]methanamine (4.7 mL) was dissolved in dichloromethane (75 mL), and the solution was cooled to 0° C. To this solution was added dropwise a solution (10 mL) of ethyl propiolate (1.55 mL) in dichloromethane, and acetic acid (0.1 mL) was further added. The mixed solution was stirred for 4 hr while gradually warming to room temperature. The reaction solution was added to saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane) to give the object product as a pale-yellow oil (1.37 g). The obtained compound was used for the next reaction without purification.

1. additionwas further added
2. temperaturewhile gradually warming to room temperature
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with saturated brine
5. dry with materialdried over sodium sulfate
6. filtrationThe desiccant was filtered off
7. concentrationthe filtrate was concentrated
8. customThe residue was purified by silica gel column chromatography (20% ethyl acetate/hexane)

ORD record

ord-cf340f36c14844d38d18c5d08afa89b0

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575167B2