Ammonium Chloride → methyl 5-(hydroxymethyl)-1-methyl-1H-pyrrole-2-carboxylate

HRID 1009474ノート

反応式

HRID 1009474 の反応式
[CH:1]([C:3]1[N:7]([CH3:8])[C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+].[Cl-].[NH4+]>C1COCC1>[OH:2][CH2:1][C:3]1[N:7]([CH3:8])[C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 12459974methyl 5-formyl-1-methyl-1H-pyrrole-2-carboxylate

生成物 1

HCID 58009357methyl 5-(hydroxymethyl)-1-methyl-1H-pyrrole-2-carboxylate収率 87.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

670 mg of methyl 5-formyl-1-methyl-1H-pyrrole-2-carboxylate was dissolved in 10.0 mL of THF, and 303 mg of sodium borohydride was added thereto at −20° C., followed by stirring at −20° C. for 30 minutes, and then at 0° C. for further 1 hour. To the reaction liquid was added an aqueous saturated ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution and brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 592 mg of methyl 5-(hydroxymethyl)-1-methyl-1H-pyrrole-2-carboxylate.

後処理

  1. customat −20° C.
  2. waitat 0° C. for further 1 hour
  3. customTo the reaction liquid
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-1083655ced704d539f6868bc191c9cc1
出典データセット
uspto-grants-2011_07
特許番号
US07973078B2

反応ノート

読み込み中…