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

HRID 18065

反応式

HRID 18065 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1ff1cf8dc3044664b62f6f776d19baa5
出典データセット
uspto-grants-2010_06
特許番号
US07741316B2

関連ノート

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