Felbinac ethyl → Diethyl 2-(4-Biphenylyl)malonate

HRID 1249678Notes

Reaction equation

HRID 1249678 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na]>C(OC(=O)OCC)C>[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 26436Felbinac ethylHCID 5360545Sodium

Product 1

HCID 53994263Diethyl 2-(4-Biphenylyl)malonateYield 152.8%

Reagents, catalysts & solvents 1

HCID 7766Diethyl CarbonateSolvent

Conditions

Temperature
120 °C

Procedure

A solution of ethyl (4′-biphenyl)acetate (7.1 g) in 60 ml of diethylcarbonate, kept under nitrogen atmosphere, is added portionwise with sodium (0.734 g), then it is heated at 120° C. for 3 hours. The solvent is evaporated off and the residue is dissolved in 65 ml of cold water and acidified with acetic acid until pH=5-6 is reached. The aqueous phase is then extracted three times with diethyl ether and the pooled organic extracts are dried over sodium sulfate and concentrated to dryness. The residue is purified by silica gel chromatography (eluent: petroleum ether/diethyl ether 9.4:0.6) to give 7.05 g of the product. m.p. 51-53° C.

Workup

  1. customThe solvent is evaporated off
  2. dissolutionthe residue is dissolved in 65 ml of cold water
  3. extractionThe aqueous phase is then extracted three times with diethyl ether
  4. dry with materialthe pooled organic extracts are dried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue is purified by silica gel chromatography (eluent: petroleum ether/diethyl ether 9.4:0.6)

Sources & evidence

ORD record
ord-75f46264c35e43a3ac01a63d817114f1
Source dataset
uspto-grants-2002_01
Patent number
US06335332B1

Reaction notes

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