HCID 66748006, compound → Ethyl 4-(4-chlorophenyl)-3-oxobutanoate

HRID 2401753Notes

Reaction equation

HRID 2401753 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[C:11]2C(=O)O[C:14](C)([CH3:18])[O:13][C:12]2=[O:20])[OH:10])=[CH:4][CH:3]=1>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9](=[O:10])[CH2:11][C:12]([O:13][CH2:14][CH3:18])=[O:20])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 66748006HCID 66748006, compound

Product 1

HCID 10847663Ethyl 4-(4-chlorophenyl)-3-oxobutanoateYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-(2-(4-chlorophenyl)-1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (103 g, 347 mmol) in ethanol (718 mL) was refluxed for 3 hours. The reaction was cooled and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/hexane=0/100→20/80) to give 61 g of the title compound as an orange oil. (73% yield). LC/MS (FA) ES+ 241. 1H NMR (400 MHz, CDCl3) δ: 7.32-7.28 (m, 2H), 7.15-7.11 (m, 2H), 4.17 (q, 2H, J=7.2 Hz), 3.81 (s, 2H), 3.45 (s, 2H), 1.26 (t, 3H, J=7.2 Hz).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel chromatography (ethyl acetate/hexane=0/100→20/80)

Sources & evidence

ORD record
ord-54fdf4b1a7c84990a217ec2638d2ed28
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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