Triethylamine → Ibuprofen methyl ester

HRID 1906054Notes

Reaction equation

HRID 1906054 reaction equation
CO[C:3](OC)([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:9][CH:8]=1)[CH:4](O)C.[CH2:19](N(CC)CC)C.S(Cl)(Cl)(=O)=O.[C:31](=[O:34])([O-])[OH:32].[Na+]>C(Cl)Cl>[CH2:13]([C:10]1[CH:9]=[CH:8][C:7]([CH:3]([CH3:4])[C:31]([O:32][CH3:19])=[O:34])=[CH:12][CH:11]=1)[CH:14]([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 13504793HCID 13504793, compound

Product 1

HCID 109101Ibuprofen methyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In this example, 2.52 g of α-hydroxy-p-isobutylpropiophenone dimethylacetal and 2.02 g of triethyl amine were dissolved in 50 ml of methylene chloride. To the solution was added 1.75 ml of sulfuryl chloride at -50° C. The mixture was stirred at the same temperature for 3 hours. Then, 20 ml of a saturated aqueous sodium hydrogen carbonate solution was added to the mixture followed by fractionation. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting oily residue was purified in a manner similar to Example 1 to obtain 1.85 g of methyl 2-(4-isobutylphenyl)propionate (yield 84%).

Workup

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting oily residue was purified in a manner similar to Example 1

Sources & evidence

ORD record
ord-8f514dbdda684660ab26dd05a6243bd6
Source dataset
uspto-grants-1987_03
Patent number
US04649213

Reaction notes

Loading…