Methyl acetoacetate → HCID 13461920, compound

Methyl acetoacetate (20.00 g, 172.2 mmol) was treated with sodium methoxide (NaOMe)/MeOH (freshly prepared by dissolving 4.00 g sodium in 200 mL anhydrous MeOH at 0° C.) at room temperature for 20 minutes. n-Heptyl bromide (24.60 mL, 156.6 mmol, 0.9 equiv.) was added and the solution was refluxed for 24 hours. Methanol was evaporated and the residue was treated with 5% hydrogen sulfate (H2SO4) (100 mL) in acetone (200 mL) at room temperature for 2 hours. Acetone was evaporated and the aqueous layer was extracted with ether (400 mL). The ether extract was then quickly washed with 1N NaOH (100 mL×3), water (100 mL×2), and brine (100 mL×1), and dried over MgSO4. Evaporation of the solvents yielded 33.56 g (78%) crude product as an oil. Rf =0.6 (10% ether/petroleum ether). 1H NMR (400 MHz, CDCl3) δ 0.88 (3 H, t, J=6.7 Hz), 1.20-1.45 (10 H, br m), 1.78-1.91 (2 H, m), 2.22 (3 H, s), 3.42 (1 H, t, J=7.4 Hz), 3.73 (3 H, s).

1. customfreshly prepared
2. temperaturethe solution was refluxed for 24 hours
3. customMethanol was evaporated
4. additionthe residue was treated with 5% hydrogen sulfate (H2SO4) (100 mL) in acetone (200 mL) at room temperature for 2 hours
5. customAcetone was evaporated
6. extractionthe aqueous layer was extracted with ether (400 mL)
7. extractionThe ether extract
8. washwas then quickly washed with 1N NaOH (100 mL×3), water (100 mL×2), and brine (100 mL×1)
9. dry with materialdried over MgSO4
10. customEvaporation of the solvents

ORD record

ord-7a264f17910d4e5e840ea0de8a312526

Source dataset

uspto-grants-1998_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05840698