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

HRID 1009474노트

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HRID 1009474 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-20 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1083655ced704d539f6868bc191c9cc1
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973078B2

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