Methyl iodide → HCID 20556706, compound

HRID 1660455Notes

Reaction equation

HRID 1660455 reaction equation
[CH3:1][S:2][CH:3]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=2)[CH:9]=1)[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[CH3:22]I.[Cl-].[NH4+]>CN(C)C=O>[CH3:1][S:2][C:3]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][CH3:19])[CH:14]=2)[CH:9]=1)([CH3:22])[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 20556694HCID 20556694, compound

Product 1

HCID 20556706HCID 20556706, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl α-methylthio-α-(6-methoxy-2-naphthyl)acetate (420 mg) was dissolved in 5 ml of dimethylformamide, and 60 mg (65% content) of sodium hydride was added. The mixture was stirred at room temperature for 10 minutes. Then, 0.20 ml of methyl iodide was added, and the mixture was stirred at room temperature for 30 minutes. An aqueous solution of ammonium chloride (0.5g/30ml) was added and the mixture was extracted three times with 20 ml of diethyl ether. The organic layer was washed twice with 10 ml of water and dried over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was chromatographed on a silica gel using benzene as an eluent to afford 378 mg of methyl α-methylthio-α-(6-methoxy-2-naphthyl)propionate in a yield of 86%.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. extractionthe mixture was extracted three times with 20 ml of diethyl ether
  3. washThe organic layer was washed twice with 10 ml of water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated off under reduced pressure
  6. customthe residue was chromatographed on a silica gel

Sources & evidence

ORD record
ord-07b2d12d6db549f9b8bd8d14f9badc35
Source dataset
uspto-grants-1981_12
Patent number
US04308208

Reaction notes

Loading…