Acetic Acid → Ethyl 2-benzyl-3-oxopropanoate

HRID 705823

반응식

HRID 705823 반응식
[H-].[Na+].[C:3]1([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:16](OCC)=[O:17].C(O)(=O)C>COCCOC>[CH:16]([CH:10]([CH2:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:17]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 8025Ethyl formateHCID 16237Ethyl 3-phenylpropionateHCID 24758Sodium hydride

생성물 1

HCID 562571Ethyl 2-benzyl-3-oxopropanoate수율 100%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매2회

실험 절차

To a suspension of NaH (2.338 g, 58.5 mmol) in DME (20 mL) was added dropwise a solution of ethyl 3-phenylpropanoate (3.2 g, 19.49 mmol) and ethyl formate (6.28 mL, 78 mmol) in DME (20 mL) at room temperature. The reaction mixture was then stirred overnight. It was neutralized with acetic acid (4 mL), then extracted with EtOAc. The organic phase was collected, washed with brine, dried over Na2SO4, filtered, and concentrated affording the crude title compound (4.02 g, 100% yield). LCMS: rt=2.82 and 3.51 min (a mixture of ketone and enol isomer), [M+H+]=207.1

후처리

  1. extractionextracted with EtOAc
  2. customThe organic phase was collected
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7f8a389c3bc0491d9d17997fc27404b0
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174968B2

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