Methyl iodide → HCID 68957574, compound

HRID 1784951Notes

Reaction equation

HRID 1784951 reaction equation
[C:1]([S:4][CH2:5][C:6]1[CH:7]=[C:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:9]=[C:10]([CH:16]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])(=O)C.C[O-].[Na+].CI>C1COCC1.CO>[CH3:1][S:4][CH2:5][C:6]1[CH:7]=[C:8]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:9]=[C:10]([CH:16]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 86612602HCID 86612602, compound

Product 1

HCID 68957574HCID 68957574, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To diethyl 5-(acetylthiomethyl)isophthalate (1.02 gm, 3.30 mmol) in THF (10 ml) and MeOH (10 ml), sodium methoxide (207 mg, 3.63 mmol) was added and stirred at rt for 2 h. Then methyl iodide (0.69 ml, 10.9 mmol) were added in two portions. After stirring at rt for 4 h, THF and MeOH were removed in vacuum and the reaction mixture was diluted with ethyl acetate. Organic layer was washed with water, brine and dried. Column purification of the crude residue yielded diethyl 5-(methylthiomethyl)isophthalate in 55% yield.

Workup

  1. stirringAfter stirring at rt for 4 h
  2. customTHF and MeOH were removed in vacuum
  3. additionthe reaction mixture was diluted with ethyl acetate
  4. washOrganic layer was washed with water, brine
  5. customdried
  6. customColumn purification of the crude residue

Sources & evidence

ORD record
ord-73a9c2b7f338443691adff10ef1e88f8
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Reaction notes

Loading…