Diethyl (ethoxymethylene)malonate → HCID 86613888, compound

Temperature

-20 °C

Diisopropylamine (1.6 mL, 11.6 mmol) in tetrahydrofuran (15 mL) was charged with n-butyllithium (2.5M, 4.6 mL, 11.6 mmol) at 0° C. The reaction stirred for 0.5 h. The solution was cooled to −20° C. and (6-mesitylpyridin-2-yl)acetonitrile (2.49 g, 10.5 mmol) was added drop wise (as a solution in 5 mL tetrahydrofuran). After 0.5 h, the solution was cooled to −78° C. and diethyl ethoxymethylenemalonate (2.1 mL, 10.5 mmol) was added. The reaction stirred for 0.5 h and was then cooled to room temperature. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated to give an orange residue. The material was dissolved in acetic acid (20 mL) and heated at 100° C. for 4 h. The solution was cooled and poured into an Erlenmeyer flask and washed with water. The solution was neutralized with saturated sodium bicarbonate. The solution was extracted with ethyl acetate (3 times), dried, and concentrated. Flash chromatography (25% ethyl acetate/hexanes) gave 3.19 g (84% yield) of the title compound as a yellow solid.

1. waitAfter 0.5 h
2. temperaturethe solution was cooled to −78° C.
3. stirringThe reaction stirred for 0.5 h
4. temperaturewas then cooled to room temperature
5. customThe reaction was quenched with water
6. extractionextracted with ethyl acetate
7. dry with materialThe organic layer was dried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customto give an orange residue
11. temperatureheated at 100° C. for 4 h
12. temperatureThe solution was cooled
13. additionpoured into an Erlenmeyer flask
14. washwashed with water
15. extractionThe solution was extracted with ethyl acetate (3 times)
16. customdried
17. concentrationconcentrated

ORD record

ord-80cd84f48efa4ab0a310ed7675d60ed9

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07897607B2