Dimethylformamide → HCID 58755279, compound

To an ice-cooled solution of triethyl 4-phosphonocrotonate (24.0 g, 95.9 mmol) in tetrahydrofuran (100 mL) was added by small portions sodium hydride (60% in oil, 3.84 g, 96.0 mmol), and the mixture was stirred under nitrogen atmosphere for 30 min. A solution of 3-methoxybenzaldehyde (12.3 g, 90.0 mmol) in tetrahydrofuran (100 mL) was added dropwise to the reaction mixture and the mixture was stirred at room temperature for 2 hr. N,N-Dimethylformamide (50 mL) was added and the mixture was further stirred for 18 hr. The reaction mixture was concentrated under reduced pressure, and 1 M hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10%-30% ethyl acetate/hexane) to give the title compound (7.70 g, yield 37%) as a yellow oil.

1. stirringthe mixture was stirred at room temperature for 2 hr
2. stirringthe mixture was further stirred for 18 hr
3. concentrationThe reaction mixture was concentrated under reduced pressure, and 1 M hydrochloric acid
4. additionwas added
5. extractionthe mixture was extracted with ethyl acetate
6. dry with materialThe extract was dried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (10%-30% ethyl acetate/hexane)

ORD record

ord-ae7dc23270414bd58b51248ce78852c3

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07820837B2