Methyl vinyl ketone → 4,4-Bis(3-fluorophenyl)cyclohexenone

HRID 1029935노트

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HRID 1029935 반응식
[CH3:1][C:2](=[O:5])[CH:3]=[CH2:4].[F:6][C:7]1[CH:8]=[C:9]([CH:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[CH:14]=O)[CH:10]=[CH:11][CH:12]=1.[OH-].[K+]>C(OCC)C.C(O)C.C(OCC)(=O)C.O>[F:6][C:7]1[CH:8]=[C:9]([C:13]2([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[CH2:14][CH2:1][C:2](=[O:5])[CH:3]=[CH:4]2)[CH:10]=[CH:11][CH:12]=1

참가 물질

8

반응물 3

HCID 6570Methyl vinyl ketoneHCID 14797Potassium HydroxideHCID 54068354HCID 54068354, 화합물

생성물 1

HCID 543073284,4-Bis(3-fluorophenyl)cyclohexenone

시약·촉매·용매 4

HCID 702Ethanol용매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

Butenone (50.4 cc) is added to a solution of bis-(3-fluorophenyl)acetaldehyde (144.5 g) in ethyl ether (500 cc) and then, after cooling to 0° C., a solution of potassium hydroxide (13.9 g) in ethanol (89 cc) is added dropwise. The reaction mixture is stirred for 2 h at 0° C. and then for 16 hours at 25° C. and diluted with ethyl acetate (300 cc) and water (500 cc). The aqueous phase is washed with ethyl acetate (300 cc). The combined organic phases are washed with saturated sodium chloride solution (500 cc), dried over magnesium sulphate and concentrated under reduced pressure (2.7 kPa). The residue is chromatographed (in two passes) on silica gel (particle size 0.04-0.063 mm, columns 8.5 cm in diameter and 34 cm high), eluting under a nitrogen pressure of 0.5 bar with a mixture of cyclohexane and ethyl acetate (90/10). 4,4-bis-(3-Fluorophenyl)-cyclohexenone (90.3 g) is obtained in the form of white crystals. m.p.=95° C.

후처리

  1. waitfor 16 hours at 25° C.
  2. washThe aqueous phase is washed with ethyl acetate (300 cc)
  3. washThe combined organic phases are washed with saturated sodium chloride solution (500 cc)
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure (2.7 kPa)
  6. customThe residue is chromatographed (in two passes) on silica gel (particle size 0.04-0.063 mm, columns 8.5 cm in diameter and 34 cm high)
  7. washeluting under a nitrogen pressure of 0.5 bar
  8. additionwith a mixture of cyclohexane and ethyl acetate (90/10)

출처 및 근거

ORD 기록
ord-c72e6252e77d42bda61bdea4f6c0e687
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05102667

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