Methacryloyl chloride → (E)-N-methacryloylbut-2-enamide

Experimental Procedure: To a suspension of (E)-but-2-enamide (1.0 equiv) in 3.5 mL THF was added n-BuLi in hexanes (2.5 M,1.2 equiv) slowly at −78° C. The reaction mixture was warmed up to room temperature and stirred for 8 h before a solution of methacryloyl chloride (2.0 equiv) in 2 mL of THF was added drop wise at −78° C. The reaction mixture was allowed to warm up to rt overnight. The crude reaction mixture was diluted with ethyl acetate, and quenched with cold NH4Cl(aq, sat), and the organic layer separated. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine and dried over MgSO4. After filtration and evaporation under reduced pressure, the residue was purified by column chromatography to yield the pure compound.

1. additionwas added drop wise at −78° C
2. temperatureto warm up to rt overnight
3. customThe crude reaction mixture
4. customquenched with cold NH4Cl(aq, sat)
5. customthe organic layer separated
6. extractionThe aqueous layer was extracted twice with ethyl acetate
7. washThe combined organic layers were washed with brine
8. dry with materialdried over MgSO4
9. filtrationAfter filtration and evaporation under reduced pressure
10. customthe residue was purified by column chromatography
11. customto yield the pure compound

ORD 기록

ord-b6e713ba9a044e2b97d5ba2a0a95dbc8

출처 데이터셋

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09108923B2