Tetrahydrofuran → HCID 69206973, compound

Temperature

-78 °C

Potassium bis(trimethylsilyl)amide (20% toluene solution, 1.0 g) was added to a mixture of bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl) phosphonate (318 mg), 18-crown-6 (1.32 g) and tetrahydrofuran (20 mL) at −78° C. Then 5-(4-methoxyphenyl)-1-methyl-1H-pyrazole-4-carbaldehyde (216 mg) was added and the mixture was stirred at −78° C. for 4 hrs. Aqueous ammonium chloride was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. Methanol (5 mL) and a 1N aqueous sodium hydroxide solution (5 mL) were added to the residue and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was concentrated, 1N hydrochloric acid was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. Recrystallization of the residue from ethyl acetate-hexane gave (2Z)-3-[5-(4-methoxyphenyl)-1-methyl-1H-pyrazol-4-yl]acrylic acid as crystals (77 mg, yield 30%). melting point: 205-206° C.

1. extractionthe mixture was extracted with ethyl acetate
2. washThe organic layer was washed successively with water and saturated brine
3. dry with materialdried over anhydrous magnesium sulfate
4. concentrationconcentrated
5. additionMethanol (5 mL) and a 1N aqueous sodium hydroxide solution (5 mL) were added to the residue
6. stirringthe mixture was stirred at 60° C. for 1 hr
7. concentrationThe reaction mixture was concentrated
8. addition1N hydrochloric acid was added to the residue
9. extractionthe mixture was extracted with ethyl acetate
10. washThe organic layer was washed successively with water and saturated brine
11. dry with materialdried over anhydrous magnesium sulfate
12. concentrationconcentrated
13. customRecrystallization of the residue from ethyl acetate-hexane

ORD record

ord-d0332032eb2842d9bc88493d3904a94b

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07423159B2