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

HRID 77656

반응식

HRID 77656 반응식
[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

참가 물질

6

반응물 4

HCID 180AcetoneHCID 962WaterHCID 14798Sodium HydroxideHCID 680093-Fluorobenzaldehyde

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b896188ea0824f719c74a4f42878ee58
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841326B2

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