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Acetone → 5-[(6-Bromo-2-pyridyl)-methyl]-tetrahydrofuran-2-one

HRID 1756346
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인쇄 미리보기

반응식

HRID 1756346 반응식
C[O:2][C:3](=[O:16])[CH2:4][CH2:5][C:6](=O)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[N:9]=1.[BH4-].[Na+].CC(C)=O>CO>[Br:14][C:10]1[N:9]=[C:8]([CH2:7][CH:6]2[O:16][C:3](=[O:2])[CH2:4][CH2:5]2)[CH:13]=[CH:12][CH:11]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 156617995-(6-Bromo-2-pyridyl)-4-oxo-pentanoic acid methyl ester

생성물 1

HCID 199664915-[(6-Bromo-2-pyridyl)-methyl]-tetrahydrofuran-2-one수율 96%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
1.5 °C
이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

실험 절차

A solution of 490 mg of 5-(6-bromo-2-pyridyl)-4-oxo-pentanoic acid methyl ester in 20 ml of methanol is mixed under ice cooling with 72 mg of sodium borohydride and stirred for 1 hour at 0-3° C. Then, 2 ml of acetone is added, stirred for 1 more hour and the reaction mixture is evaporated to dryness. The residue is distributed between water and ethyl acetate, the organic phase is dried on sodium sulfate and concentrated by evaporation. 421 mg of 5-[(6-bromo-2-pyridyl)-methyl]-tetrahydrofuran-2-one is obtained as yellow oil.

후처리

  1. stirringstirred for 1 more hour
  2. customthe reaction mixture is evaporated to dryness
  3. customthe organic phase is dried on sodium sulfate
  4. concentrationconcentrated by evaporation

출처 및 근거

ORD 기록
ord-9ebf860b826341cd9a1c7c947556ae6d
출처 데이터셋
uspto-grants-1995_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05440044

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