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

HRID 48062

反応式

HRID 48062 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0ae043e1bfba43f78f3d7cfab4c39611
出典データセット
uspto-grants-2004_03
特許番号
US06699898B2

関連ノート

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