1-Diethoxyphosphorylpropan-2-one → 4-[3-(Trifluoromethoxy)phenyl]-3-buten-2-one

HRID 48062

반응식

HRID 48062 반응식
[OH-].[Na+].[F:3][C:4]([F:15])([F:14])[O:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=O.[O:16]=[C:17]([CH3:27])[CH2:18]P(=O)(OCC)OCC>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[F:3][C:4]([F:15])([F:14])[O:5][C:6]1[CH:7]=[C:8]([CH:9]=[CH:18][C:17](=[O:16])[CH3:27])[CH:11]=[CH:12][CH:13]=1

참가 물질

6

반응물 3

HCID 140281-Diethoxyphosphorylpropan-2-oneHCID 14798Sodium HydroxideHCID 6051393-(Trifluoromethoxy)benzaldehyde

생성물 1

HCID 693441184-[3-(Trifluoromethoxy)phenyl]-3-buten-2-one수율 54%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6344Dichloromethane용매2회

실험 절차

Ex-626A) Tetrabutylammonium iodide (0.4 g, 0.05 mol) was added to a well-stirred biphasic mixture of 12 mL of 50% NaOH and 20 mL of methylene chloride under a nitrogen atmosphere. A solution of 3-trifluoromethoxybenzaldehyde (4.0 g, 0.021 mol) and diethyl (2-oxopropyl)phosphonate (4.08 g, 0.021 mol) in 4.0 mL of methylene chloride was added dropwise to the stirred solution. The resulting mixture was stirred at room temperature for 15 min, then quenched with water and extracted with hexane. The hexane layer was dried over MgSO4. The crude product was purified by flash column chromatography on silica gel eluting with 1:10 ethyl acetate in hexane to give 2.6 g (54%) of the desired 4-[3-(trifluoromethoxy)phenyl]-3-buten-2-one product as a yellow oil. 1H NMR (CDCl3) δ7.43 (m, 4H), 7.20 (d, 1H), 6.65 (d, 2H), 2.29 (s, 3H). 19F NMR (CDCl3) δ−62.05 (s, 3F).

후처리

  1. customquenched with water
  2. extractionextracted with hexane
  3. dry with materialThe hexane layer was dried over MgSO4
  4. customThe crude product was purified by flash column chromatography on silica gel eluting with 1:10 ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-0ae043e1bfba43f78f3d7cfab4c39611
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699898B2

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