Hydrochloric Acid → Ethyl 2-(4-fluorobenzoyl)-3-oxo-4-phenylbutanoate

HRID 860412

반응식

HRID 860412 반응식
[Cl-].[Mg+2].[Cl-].[O:4]=[C:5]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.Cl>O1CCCC1.C(OCC)(=O)C.N1C=CC=CC=1>[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([CH:6]([C:5](=[O:4])[CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:25])=[CH:22][CH:21]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 678794-Fluorobenzoyl chlorideHCID 225855Ethyl 3-oxo-4-phenylbutanoateHCID 5360315Magnesium Chloride

생성물 1

HCID 57444525Ethyl 2-(4-fluorobenzoyl)-3-oxo-4-phenylbutanoate수율 67.5%

시약·촉매·용매 3

HCID 1049Pyridine용매HCID 8028Tetrahydrofuran용매3회HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a suspensin of magnesium chloride (1.46 g) in tetrahydrofuran (10 ml) was added a solution of ethyl 3-oxo-4-phenylbutanoate (2.0 g) in tetrahydrofuran (10 ml) and the mixture was cooled to 0° C., then pyridine (2.5 ml) was added. The mixture was stirred at 20° C. for 30 minutes, then a solution of 4-fluorobenzoyl chloride (2.44 g) in tetrahydrofuran (10 ml) was added at 0° C. After stirring at 20° C. for 2 hours, the mixure was partitoned between 0.5N hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:5) to give ethyl 2-(4-fluorobenzoyl)-3-oxo-4-phenylbutanoate (2.15 g) as an oil.

후처리

  1. stirringAfter stirring at 20° C. for 2 hours
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:5)

출처 및 근거

ORD 기록
ord-6e2cc6132f9e4460b2e12f9e04928393
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153854B2

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