Ethyl 2-thiopheneglyoxylate → Ethyl 2-hydroxy-2-(thiophen-2-yl)acetate

HRID 77012

反応式

HRID 77012 の反応式
[O:1]=[C:2]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[BH4-].[Na+]>C(O)C>[CH2:6]([O:5][C:3](=[O:4])[CH:2]([OH:1])[C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[CH3:7]

参加物

4

反応物 2

HCID 77693Ethyl 2-thiopheneglyoxylateHCID 4311764Sodium borohydride

生成物 1

HCID 12266229Ethyl 2-hydroxy-2-(thiophen-2-yl)acetate収率 100.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of ethyl 2-oxo-2-(thiophen-2-yl)acetate (5.00 g, 27.1 mmol) in ethanol (50 mL) is cooled at 0° C. with an ice bath. NaBH4 (0.31 g, 8.14 mmol) is added in four portions under stirring. The mixture is stirred at 0° C. for 10 minutes, then allowed to warm at RT and stirred for additional 30 minutes. Reaction is concentrated under vacuum and the residue is partitioned between Et2O and ice-cooled water. The organic layer is separated, washed with water and brine, dried over Na2SO4, filtered and evaporated to give a colorless liquid (5.05 g, 91% yield).

後処理

  1. stirringThe mixture is stirred at 0° C. for 10 minutes
  2. stirringstirred for additional 30 minutes
  3. customReaction
  4. concentrationis concentrated under vacuum
  5. customthe residue is partitioned between Et2O and ice-
  6. temperaturecooled water
  7. customThe organic layer is separated
  8. washwashed with water and brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customevaporated

出典と根拠

ORDレコード
ord-f30f4557d680473d9c27cb850dc26929
出典データセット
uspto-grants-2014_09
特許番号
US08835682B2

関連ノート

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