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Sodium hydride → methyl 4-[(E)-1-(4-fluorobenzoyl)-4-phenyl-3-butenyl]benzoate

HRID 1371049
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HRID 1371049 반응식
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[O:12])=[CH:6][CH:5]=1.[H-].[Na+].[CH2:23](Br)[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[F:19][C:16]1[CH:15]=[CH:14][C:13]([C:11]([CH:10]([C:7]2[CH:6]=[CH:5][C:4]([C:3]([O:2][CH3:1])=[O:20])=[CH:9][CH:8]=2)[CH2:23]/[CH:24]=[CH:25]/[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:12])=[CH:18][CH:17]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 98116BromomethylstyreneHCID 18510220Methyl 4-[2-(4-fluorophenyl)-2-oxoethyl]benzoate

생성물 1

HCID 18510204methyl 4-[(E)-1-(4-fluorobenzoyl)-4-phenyl-3-butenyl]benzoate수율 72.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

To a solution of methyl 4-[2-((4-fluorophenyl)-2-oxoethyl]benzoate (Example 1, Step 2) (1.0 g, 3.67 mmole) in DMF (10 mL) at 0° C. was added NaH (0.105 mg, 3.6 mmol). After stirring for 10 minutes at 0° C., cinnamyl bromide (0.71 g, 3.6 mmole) was added to the mixture. The reaction was stirred for r.t. for 1 h. and was then quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic phase dried (Na2SO4), filtered, and evaporated. The residue was purified by flash chromatography to yield 1.02 g of the desired product.

후처리

  1. stirringThe reaction was stirred for r.t. for 1 h.
  2. customwas then quenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-8c4d165366464f9792c0369fe085d445
출처 데이터셋
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06583126B2

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