Acetone → 1,5-Bis(3-fluorophenyl)-1,4-pentadien-3-one

HRID 714171ノート

反応式

HRID 714171 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:10][C:11]([CH3:13])=[O:12].[OH-].[Na+].O>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:10][C:11](=[O:12])[CH:13]=[CH:5][C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[CH:3]=2)[CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 4

HCID 180AcetoneHCID 962WaterHCID 14798Sodium HydroxideHCID 680093-Fluorobenzaldehyde

生成物 1

HCID 695017221,5-Bis(3-fluorophenyl)-1,4-pentadien-3-one収率 42%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

3-Fluorobenzaldehyde (1s, 0.5 ml, 4.7 mmol) and acetone (19, 0.18 ml, 2.3 mmol) were combined in ethanol (20 ml) and stirred for 10 min at room temperature. A solution of sodium hydroxide (0.29 g, 7.3 mmol) and water (15 ml) was added and the mixture stirred for 18 hr at room temperature. The resulting mixture was filtered and chromatographed on silica gel with ethyl acetate/hexane to give a solid. The crude was recrystallized from ethanol to afford 0.26 g (42%) of yellow crystals: mp 96-97° C. [expected mp 96-97° C.]; 1H NMR: δ 7.03 (d, 2H, J=16.1 Hz), 7.09 (m, 2H), 7.35 (m, 6H), 7.67 (d, 2H, J=15.9 Hz); 13C NMR: δ 114.4, 117.5, 124.4, 126.3, 130.4, 136.9, 142.0, 162.9, 188.1; Anal. Calcd for C17H12OF2: C, 75.55; H, 4.48. Found: C, 75.26; H, 4.65.

後処理

  1. stirringthe mixture stirred for 18 hr at room temperature
  2. filtrationThe resulting mixture was filtered
  3. customchromatographed on silica gel with ethyl acetate/hexane
  4. customto give a solid
  5. customThe crude was recrystallized from ethanol

出典と根拠

ORDレコード
ord-6ac76e8e1e11405c82345397eaae86a8
出典データセット
uspto-grants-2015_11
特許番号
US09187397B2

反応ノート

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