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

HRID 570124Notes

Reaction equation

HRID 570124 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1)=[O:3].[CH2:11]([O:13][C:14](=O)[O:15]CC)[CH3:12].[H-].[Na+]>C(O)C>[F:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH2:1][C:14]([O:13][CH2:11][CH3:12])=[O:15])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 98284'-FluoroacetophenoneHCID 24758Sodium hydride

Product 1

HCID 2758844Ethyl 3-(4-Fluorophenyl)-3-OxopropanoateYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 4-fluoroacetophenone (20.0 g, 0.145 mol), ethanol (1 mL) and diethylcarbonate (100 mL) is added sodium hydride (60%, 12.0 g, 0.29 mol) at 0° C. portionwise over a period of 30 min. Afterwards the reaction mixture is allowed to warm to room temperature and stirred for 3 h. Thereafter, the reaction is quenched with aqueous 10% HCl and extracted with ethyl acetate (2×100 mL). The ethyl acetate layer is dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The crude material is purified by column chromatography using silica gel (230-400 mesh) in ethyl acetate and hexane (1:99 to 5:95) as eluent and 25 g (83%) of ethyl 3-(4-fluorophenyl)-3-oxopropanoate are obtained as light yellow liquid.

Workup

  1. customThereafter, the reaction is quenched with aqueous 10% HCl
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. dry with materialThe ethyl acetate layer is dried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material is purified by column chromatography

Sources & evidence

ORD record
ord-7cc2b35debf2454a9143f34c10237ba5
Source dataset
uspto-grants-2015_05
Patent number
US09023844B2

Reaction notes

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