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

HRID 18065

반응식

HRID 18065 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1ff1cf8dc3044664b62f6f776d19baa5
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741316B2

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