Methyl iodide → Methyl 2-phenylthio-2-(3-phenoxyphenyl)propionate

HRID 1733619Notes

Reaction equation

HRID 1733619 reaction equation
[C:1]1([S:7][CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:14]=2)[C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:28]I.[Cl-].[NH4+]>CN(C)C=O>[C:1]1([S:7][C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:14]=2)([CH3:28])[C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 23453441Methyl alpha-phenylthio(m-phenoxyphenyl)acetate

Product 1

HCID 20556693Methyl 2-phenylthio-2-(3-phenoxyphenyl)propionateYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl α-phenylthio(m-phenoxyphenyl)acetate (521 mg) was dissolved in 2 ml of anhydrous dimethylformamide. After cooling with ice, 65 mg (65% content) of sodium hydride was added, and the mixture was stirred for 30 minutes. Then, 0.15 ml of methyl iodide was added, and the mixture was stirred for 5 minutes with ice cooling and then for 2 hours at room temperature. After an aqueous solution of ammonium chloride (1 g/40 ml) was added, the mixture was extracted three times with 40 ml of diethyl ether. The organic layer was washed twice with 20 ml of water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using benzene as an eluent to afford 522 mg of methyl α-phenylthio-α-(m-phenoxyphenyl)propionate as an oil in a yield of 96%.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 5 minutes with ice cooling
  3. waitfor 2 hours at room temperature
  4. extractionthe mixture was extracted three times with 40 ml of diethyl ether
  5. washThe organic layer was washed twice with 20 ml of water
  6. dry with materialdried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-cb33ff81c84746c4a17e22256b729238
Source dataset
uspto-grants-1980_12
Patent number
US04242519

Reaction notes

Loading…