HCID 20556706, compound → (RS)-Naproxen methyl ester

HRID 1660456Notes

Reaction equation

HRID 1660456 reaction equation
CS[C:3]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[CH:10]=1)([CH3:8])[C:4]([O:6][CH3:7])=[O:5]>CO.[Ni]>[CH3:20][O:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([CH:3]([CH3:8])[C:4]([O:6][CH3:7])=[O:5])[CH:18]=[CH:17]2

Participants

4

Reactant 1

HCID 20556706HCID 20556706, compound

Product 1

HCID 529084(RS)-Naproxen methyl esterYield 68%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

Methyl α-methylthio-α-(6-methoxy-2-naphthyl)propionate (372 mg) was dissolved in 2 ml of methanol, and 10 ml of a methanol suspension of 5.0 cc of Raney nickel (W-II) was added, and the mixture was stirred at room temperature for 15 hours. The insoluble matter was separated by filtration, and the filtrate was concentrated under reduced pressure. Methylene chloride was added to the residue. The insoluble matter was separated by filtration. The filtrate was concentrated under reduced pressure, and the residue was chromatographed on a silica gel column using benzene as an eluent to afford 212 mg of methyl α-(6-methoxy-2-naphthyl)propionate as colorless crystals in a yield of 68%. The product had a melting point (from petroleum ether) of 67° to 69° C. The IR and NMR spectra of this product coincided with those of the authentic sample.

Workup

  1. additionwas added
  2. customThe insoluble matter was separated by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionMethylene chloride was added to the residue
  5. customThe insoluble matter was separated by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-14fe8785716145c682f86fb4e166dab9
Source dataset
uspto-grants-1981_12
Patent number
US04308208

Reaction notes

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