Potassium Carbonate → Ethyl 2-((4-fluorophenyl)methyl)-3-oxo-3-(4-(trifluoromethyl)phenyl)propionate

HRID 1610472

반응식

HRID 1610472 반응식
[O:1]=[C:2]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][CH:3]([C:2](=[O:1])[C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:11][CH:10]=2)[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 2760281Ethyl 3-oxo-3-(4-(trifluoromethyl)phenyl)propanoate

생성물 1

HCID 22261408Ethyl 2-((4-fluorophenyl)methyl)-3-oxo-3-(4-(trifluoromethyl)phenyl)propionate수율 61.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

A mixture of ethyl 3-oxo-3-(4-trifluoromethylphenyl)propionate (38.2 g, 0.147 mol), 4-fluorobenzyl bromide (25 g, 0.13 mol), potassium carbonate (36.6 g, 0.26 mol) and acetonitrile (500 ml) was stirred at 60° C. for 3 hrs. The reaction solution was concentrated under reduced pressure, and water (500 ml) was added. The mixture was extracted with ethyl acetate (500, 200 ml). The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1-10:1, hexane:toluene=1:1) and crystallized from cold hexane to give ethyl 2-((4-fluorophenyl)methyl)-3-oxo-3-(4-(trifluoromethyl)phenyl)propionate (29.5 g, 55%).

후처리

  1. concentrationThe reaction solution was concentrated under reduced pressure, and water (500 ml)
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate (500, 200 ml)
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1-10:1, hexane:toluene=1:1)
  8. customcrystallized from cold hexane

출처 및 근거

ORD 기록
ord-1122205c20d345ca8b325883035c9457
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982348B2

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