Acetone → 5-(Hydroxymethyl)thiophene-2-carboxylic acid

HRID 1427050ノート

反応式

HRID 1427050 の反応式
[BH4-].[Na+].[CH:3]([C:5]1[S:9][C:8]([C:10]([OH:12])=[O:11])=[CH:7][CH:6]=1)=[O:4].CC(C)=O>CO>[OH:4][CH2:3][C:5]1[S:9][C:8]([C:10]([OH:12])=[O:11])=[CH:7][CH:6]=1

参加物

5

反応物 3

HCID 180AcetoneHCID 8188825-Formyl-2-thiophenecarboxylic AcidHCID 4311764Sodium borohydride

生成物 1

HCID 226495615-(Hydroxymethyl)thiophene-2-carboxylic acid収率 87.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Sodium borohydride (218 mg, 5.76 mmol) was added to a solution of commercially available 5-formyl-2-thiophenecarboxylic acid (599 mg, 3.84 mmol) in methanol (19 mL), and the mixture was stiffed under nitrogen atmosphere at room temperature for 4 hours and 30 minutes. Acetone was added to the reaction mixture, and the mixture was concentrated under vacuum. 2 M hydrochloric acid and ethyl acetate were added to the residue for partition, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under vacuum and the precipitate was washed with diethyl ether and n-hexane to obtain the title compound (529 mg, 87%).

後処理

  1. concentrationthe mixture was concentrated under vacuum
  2. addition2 M hydrochloric acid and ethyl acetate were added to the residue
  3. customfor partition
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under vacuum
  9. washthe precipitate was washed with diethyl ether and n-hexane

出典と根拠

ORDレコード
ord-0342813d4125457bab13cd7c1c5ca2cd
出典データセット
uspto-grants-2015_01
特許番号
US08933099B2

反応ノート

読み込み中…