Potassium Hydroxide → Ethyl 2-(4-methoxyphenyl)cyclopropanecarboxylate

Temperature

0 °C

To a 50 mL RB flask fitted with magnetic stirrer was charged with 14 mL of dimethylsulfoxide. To the stirred solvent was added trimethylsulfoxonium iodide (1.53 g, 6.93 mmol). The reaction mixture was cooled to 0° C. and powdered potassium hydroxide (0.42 g, 7.49 mmol) was added portion wise, stirred for 10 minutes at room temperature. Then ethyl (2Z)-3-(4-methoxyphenyl)-acrylate (1.3 g, 6.31 mmol) was added. The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was quenched with water and diethyl ether was added. The layers were separated and the organic layer was washed with brine solution (50 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude material was purified by silica gel column chromatography using ethyl acetate and petroleum ether as elutant. The product was obtained as pale pink solid (0.6 g, yield: 43.22%). 1H NMR (300 MHz, CDCl3): δ 6.95-6.98 (d, 2H), 6.74-6.77 (d, 2H), 4.06-4.13 (q, 2H), 3.72 (s, 3H), 2.38-2.44 (m, 1H), 1.72-1.78 (m, 1H), 1.43-1.61 (m, 2H), 1.25-1.29 (t, 3H).

1. customTo a 50 mL RB flask fitted with magnetic stirrer
2. stirringThe reaction mixture was stirred at room temperature for 3 h
3. customThe reaction mixture was quenched with water and diethyl ether
4. additionwas added
5. customThe layers were separated
6. washthe organic layer was washed with brine solution (50 mL)
7. dry with materialThe organic layer was dried over anhydrous Na2SO4
8. customthe solvent was removed under reduced pressure
9. customThe crude material was purified by silica gel column chromatography

ORD record

ord-a4bad09cb0c045ae9f6b7654175e2c1f

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278915B2