Sodium hydride → Methyl 3-[(e)-1-(4-fluorobenzoyl)-4-phenyl-3-butenyl]benzoate

HRID 1371030

반응식

HRID 1371030 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[CH2:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])=[CH:4][CH:3]=1.[CH2:21](Br)[CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[H-].[Na+].[NH4+].[Cl-]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH:9]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH2:21]/[CH:22]=[CH:23]/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:20])=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 98116BromomethylstyreneHCID 18510261Methyl 3-[2-(4-fluorophenyl)-2-oxoethyl]benzoate

생성물 1

HCID 18510225Methyl 3-[(e)-1-(4-fluorobenzoyl)-4-phenyl-3-butenyl]benzoate수율 87.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of the product from Step 1 (1.0 g, 3.7 mmol) and cinnamyl bromide (0.72 g, 3.7 mmol) in DMF (15 mL) at 0° C. under N2 was added the NaH (121 mg, 4.0 mmol, 80% in oil). After 20 min. at 0° C., the reaction was stirred for 1 h at r.t. Saturated NH4Cl (15 mL) was then added and the product was extracted with Et2O. The organic phase was washed with H2O and brine, and was then dried (MgSO4) filtered, and evaporated. The residue was purified by flash chromatography (1:10 EtOAc:hexane) to give a colourless oil (1.26 g).

후처리

  1. extractionthe product was extracted with Et2O
  2. washThe organic phase was washed with H2O and brine
  3. dry with materialwas then dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography (1:10 EtOAc:hexane)

출처 및 근거

ORD 기록
ord-1f8e870885524a499154f697da8702ca
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06583126B2

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