Hydrochloric Acid → HCID 69640946, compound

To a solution of diethyl malonate (10.0 g, 62.43 mmol) in THF (50 mL) was added sodium hydride (oil about 60%; 2.50 g, 62.43 mmol) under ice-cooling, and the mixture was stirred for 30 min. To this mixture was added a solution of diketene (2.62 g, 31.22 mmol) in THF (15 mL) under ice-cooling, and the mixture was stirred at 0° C. for 1 hr, and then at room temperature for 3 days. The reaction mixture was acidified with 1 N hydrochloric acid (70 mL) under ice-cooling, and extracted three times with ethyl acetate. The extracts were combined, washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluate, hexane:ethyl acetate=1:1) to give the title compound (1.79 g, 29%) as a pale-yellow solid.

1. temperaturecooling
2. temperaturecooling
3. stirringthe mixture was stirred at 0° C. for 1 hr
4. waitat room temperature for 3 days
5. temperaturecooling
6. extractionextracted three times with ethyl acetate
7. washwashed with brine
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by silica gel column chromatography (eluate, hexane:ethyl acetate=1:1)

ORD record

ord-553c0472c78c4564bbfb48e939b06bc0

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08907089B2