Ethyl Acetoacetate → HCID 86715644, compound

Sodium hydride (60% dispersion in mineral oil, 1.5 g, 38.4 mmol) was added in portions over 2 min to an ice-cooled, stirring solution of ethyl 3-oxobutanoate (5 g, 38.4 mmol) in dry dimethoxyethane (65 mL). After 30 min, a solution of 4-(trifluoromethyl)benzyl bromide (9.2 g, 38.4 mmol) in dry dimethoxyethane (10 mL) was added dropwise over 2 min. The flask was removed from the cooling bath. After 2 h, water (10 mL) was added. The mixture was partitioned between half-saturated aqueous sodium chloride solution (50 mL) and ethyl acetate (150 mL). The layers were separated. The organic layer was dried with magnesium sulfate and the dried solution was filtered. The filtrate was concentrated and the residue was purified by flash-column chromatography on silica gel eluting with hexanes-ethyl acetate to provide the title compound as a colorless liquid.

1. temperaturecooled
2. customThe flask was removed from the cooling bath
3. waitAfter 2 h
4. additionwater (10 mL) was added
5. customThe mixture was partitioned between half-saturated aqueous sodium chloride solution (50 mL) and ethyl acetate (150 mL)
6. customThe layers were separated
7. dry with materialThe organic layer was dried with magnesium sulfate
8. filtrationthe dried solution was filtered
9. concentrationThe filtrate was concentrated
10. customthe residue was purified by flash-column chromatography on silica gel eluting with hexanes-ethyl acetate

ORD record

ord-24def8b290304741b1fea020b219d949

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290476B2