Ibuprofen, (+-)- → Methyl (alphaR)-alpha-methyl-4-(2-methylpropyl)benzeneacetate

HRID 520732Notes

Reaction equation

HRID 520732 reaction equation
[OH:1][C:2]([CH:4]([C:6]1[CH:15]=[CH:14][C:9]([CH2:10][CH:11]([CH3:13])[CH3:12])=[CH:8][CH:7]=1)[CH3:5])=[O:3].[N+](=[CH2:18])=[N-]>C(OCC)C>[CH2:10]([C:9]1[CH:8]=[CH:7][C:6]([C@@H:4]([CH3:5])[C:2]([O:1][CH3:18])=[O:3])=[CH:15][CH:14]=1)[CH:11]([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 3672Ibuprofen, (+-)-HCID 9550Diazomethane

Product 1

HCID 5326009Methyl (alphaR)-alpha-methyl-4-(2-methylpropyl)benzeneacetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of (R) (−)-ibuprofen (3.45 g) in ethyl ether, cooled to 5° C., is treated, dropwise, with a 0.6 M solution of diazomethane in ethyl ether, up to a persistent yellow colour. The solvent is removed—under vacuum; the residual oil is purified by flash chromatography to yield 3.3 g of methyl (R) (−) 2-(4′-isobutylphenyl)-propionate.

Workup

  1. additionis treated
  2. customthe residual oil is purified by flash chromatography

Sources & evidence

ORD record
ord-3607a45b4a0f40ecb05b7f23a4f0285f
Source dataset
uspto-grants-2016_05
Patent number
US09328057B2

Reaction notes

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