Sodium methanesulfinate → Methyl 5-(methylsulfonylmethyl)thiophene-2-carboxylate

HRID 1017235Notes

Reaction equation

HRID 1017235 reaction equation
[CH3:1][S:2]([O-:4])=[O:3].[Na+].Br[CH2:7][C:8]1[S:12][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:9]=1>C(O)C>[CH3:1][S:2]([CH2:7][C:8]1[S:12][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:9]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 2733271Sodium methanesulfinateHCID 11424851Methyl 5-(bromomethyl)thiophene-2-carboxylate

Product 1

HCID 17908444Methyl 5-(methylsulfonylmethyl)thiophene-2-carboxylateYield 29.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 5-(methylsulfonylmethyl)thien-2-ylcarboxylate may be obtained in the following manner: 31.7 g of sodium methyl sulfinate are added to a solution of 73 g of methyl 5-(bromomethyl)thien-2-ylcarboxylate in 150 cm3 of ethanol and the suspension obtained is heated under reflux for 7 hours. The reaction medium is then concentrated to dryness under reduced pressure (2.7 kPa). The residue is extracted with four times 500 cm3 of ethyl acetate, the combined organic phases are washed successively with 250 cm3 of distilled water and 250 cm3 of a saturated sodium chloride solution, dried over magnesium sulfate, filtered and incompletely concentrated under reduced pressure. The solid which appears is isolated by filtration, rinsed with three times 25 cm3 of ice-cold ethyl acetate and provides 21.4 g of methyl 5-(methylsulfonylmethyl)thien-2-ylcarboxylate in the form of a cream-colored powder.

Workup

  1. customthe suspension obtained
  2. temperatureis heated
  3. temperatureunder reflux for 7 hours
  4. concentrationThe reaction medium is then concentrated to dryness under reduced pressure (2.7 kPa)
  5. extractionThe residue is extracted with four times 500 cm3 of ethyl acetate
  6. washthe combined organic phases are washed successively with 250 cm3 of distilled water and 250 cm3 of a saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationincompletely concentrated under reduced pressure
  10. customThe solid which appears is isolated by filtration
  11. washrinsed with three times 25 cm3 of ice-cold ethyl acetate

Sources & evidence

ORD record
ord-ccf288af77eb46bcb8041fe4ced7022f
Source dataset
uspto-grants-2002_11
Patent number
US06479479B2

Reaction notes

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