Diethyl Carbonate → Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate

Temperature

0 °C

A solution of 4-fluoroacetophenone (100 g, 7.239 mol) in dry THF (100 ml) was added dropwise over 2.5 hours to a refluxing slurry of hexane-washed NaH (68.3 g, 60% oil dispersion, 1.708 mol) and diethyl carbonate (176.0 ml, 1.453 mol) in dry THF (300 ml). This solution was refluxed an additional 0.5 hours, cooled (0° C.), and a solution of ethanol (50 ml) in dry THF (150 ml) was added to quench the excess NaH. 300 ml of water and 100 ml of acetic acid were added, and this mixture was extracted with ethyl acetate (3×300 ml). The combined organics were washed with saturated NaHCO3 (1×500 ml), washed with brine (2×500 ml), dried (MgSO4), concentrated under reduced pressure, and distilled at 10 mm to yield 146.3 g of the title compound.

1. temperatureThis solution was refluxed an additional 0.5 hours
2. customto quench the excess NaH
3. addition300 ml of water and 100 ml of acetic acid were added
4. extractionthis mixture was extracted with ethyl acetate (3×300 ml)
5. washThe combined organics were washed with saturated NaHCO3 (1×500 ml)
6. washwashed with brine (2×500 ml)
7. dry with materialdried (MgSO4)
8. concentrationconcentrated under reduced pressure
9. distillationdistilled at 10 mm

ORD record

ord-e9c3601d88a9471b816679a98f28af68

Source dataset

uspto-grants-1990_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04906624