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Sodium Formate → Benzhydryl 4-hydroxy-3-oxobutanoate

HRID 1719111
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HRID 1719111 반응식
[C:1]1([CH:7]([O:14][C:15](=[O:21])[CH2:16][C:17](=[O:20])[CH2:18]Br)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])=[O:23].[Na+]>CO>[C:1]1([CH:7]([O:14][C:15](=[O:21])[CH2:16][C:17](=[O:20])[CH2:18][OH:23])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 2723810Sodium FormateHCID 15080911Benzhydryl 4-bromo-3-oxobutyrate

생성물 1

HCID 24978293Benzhydryl 4-hydroxy-3-oxobutanoate수율 47.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 4-bromo-3-ketobutyric acid diphenylmethyl ester (2b, 11.4 g, 32.8 millimoles) in methanol dried with Molecular Sieves is added sodium formate (3.40 g, 50.0 millimoles), and the mixture is refluxed for 4 hours. The reaction mixture is filtered to remove solid material concentrated under reduced pressure, and extracted with ethyl acetate. The extract is washed with water, dried over magnesium sulfate and evaporated to remove the solvent. The residue is purified by chromatography over Lobar® column B using a mixture of benzene and ethyl acetate (3:1) as eluting solvent to afford the title compound (3b, 4.39 g, 47%).

후처리

  1. temperaturethe mixture is refluxed for 4 hours
  2. filtrationThe reaction mixture is filtered
  3. customto remove solid material
  4. concentrationconcentrated under reduced pressure
  5. extractionextracted with ethyl acetate
  6. washThe extract is washed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customto remove the solvent
  10. customThe residue is purified by chromatography over Lobar® column B
  11. additiona mixture of benzene and ethyl acetate (3:1)
  12. washas eluting solvent

출처 및 근거

ORD 기록
ord-eaa249dda5a74863b234449441bfd8ba
출처 데이터셋
uspto-grants-1985_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04539148

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