Sodium Iodide → Methyl 4-[(2-methoxy-2-oxoethyl)sulfanyl]butanoate

HRID 656026Notes

Reaction equation

HRID 656026 reaction equation
[Na].[SH:2][CH2:3][C:4]([O:6][CH3:7])=[O:5].[Na+].[I-].Cl[CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15]>CO>[CH3:7][O:6][C:4](=[O:5])[CH2:3][S:2][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 16907Methyl ThioglycolateHCID 76612Butanoic acid, 4-chloro-, methyl esterHCID 5360545Sodium

Product 1

HCID 18379236Methyl 4-[(2-methoxy-2-oxoethyl)sulfanyl]butanoateYield 105.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium (3.5 g, 0.15 mol) was added to methanol (150 mL) carefully. After cooling to room temperature, methyl 2-mercaptoacetate (15.6 g, 0.13 mol) was added. The mixture was stirred for 30 mins at room temperature and a little of NaI and methyl 4-chlorobutanoate (20.0 g, 0.15 mol) were added. The reaction mixture was refluxed over night. After cooling to room temperature, the solvent was removed under reduced pressure, then the residue was dissolved in CH2Cl2 (100 mL). The solution was washed with H2O (30 mL), brine (30 mL), and dried with Na2SO4. After removing the solvent, 28.3 g of the crude product was obtained (Yield: 94%).

Workup

  1. temperatureThe reaction mixture was refluxed over night
  2. temperatureAfter cooling to room temperature
  3. customthe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in CH2Cl2 (100 mL)
  5. washThe solution was washed with H2O (30 mL), brine (30 mL)
  6. dry with materialdried with Na2SO4
  7. customAfter removing the solvent

Sources & evidence

ORD record
ord-fc0abb1208594c2a9993bac20e607ae9
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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