Ethyl benzoylacetate → 2-Benzoyl-4-cyclohexyl-4-oxo-butyric acid ethyl ester

HRID 1725189Notes

Reaction equation

[CH3:1][CH2:2][O:3][C:4]([CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])=[O:5].Br[CH2:16][C:17]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:18].C(OCC)(=O)C>[Cl-].[Na+].O>[CH2:2]([O:3][C:4](=[O:5])[CH:6]([C:7](=[O:8])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:16][C:17]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:18])[CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred slurry of 1.44 g (36 mmol) sodium hydride, obtained as a 60% dispersion in mineral oil, in 45 mL anhydrous THF, at 0° C., was added dropwise 6.48 g (33.75 mmol) ethyl benzoyl acetate. The resulting slurry was stirred at 0° C. for 0.5 hr, upon which time was added dropwise the entire sample of 2-bromo-1-cyclohexyl-ethanone obtained in Step 1. The reaction was stirred at room temperature for 24 hr and poured into 0.4 L brine. The brine was shaken with ethyl acetate twice and the combined organic extracts were dried over MgSO4 and concentrated to afford 14.37 g (45.4 mmol, >100% yield) of 2-benzoyl-4-cyclohexyl-4-oxo-butyric acid ethyl ester. The product was used in the next step without further purification.

Workup

stirringThe reaction was stirred at room temperature for 24 hr
dry with materialthe combined organic extracts were dried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-5fa9e58dde6b498a8e0f733cb2695fe6
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07488832B2

Reaction notes

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