Pyridine → 5-(4-Fluorophenyl)-7-isopropyl-6-[4-(trifluoromethoxy)benzoyl]spiro[chromen-2,1'-cyclobutan]-4(3H)-one

HRID 1516724노트

반응식

HRID 1516724 반응식
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.ClCCl.N1C=CC=CC=1.[F:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[C:51]([CH:52]([OH:64])[C:53]3[CH:58]=[CH:57][C:56]([O:59][C:60]([F:63])([F:62])[F:61])=[CH:55][CH:54]=3)=[C:50]([CH:65]([CH3:67])[CH3:66])[CH:49]=[C:48]3[C:40]=2[C:41](=[O:68])[CH2:42][C:43]2([O:47]3)[CH2:46][CH2:45][CH2:44]2)=[CH:35][CH:34]=1>C(OCC)(=O)C.[OH-].[Na+]>[F:32][C:33]1[CH:34]=[CH:35][C:36]([C:39]2[C:51]([C:52](=[O:64])[C:53]3[CH:58]=[CH:57][C:56]([O:59][C:60]([F:62])([F:63])[F:61])=[CH:55][CH:54]=3)=[C:50]([CH:65]([CH3:66])[CH3:67])[CH:49]=[C:48]3[C:40]=2[C:41](=[O:68])[CH2:42][C:43]2([O:47]3)[CH2:46][CH2:45][CH2:44]2)=[CH:37][CH:38]=1

참가 물질

7

반응물 4

HCID 1049PyridineHCID 6344Dichloromethane2회HCID 159087TriacetoxyperiodinaneHCID 580029385-(4-Fluorophenyl)-6-{hydroxy[4-(trifluoromethoxy)phenyl]methyl}-7-isopropylspiro[chromen-2,1'-cyclobutan]-4(3H)-one

생성물 1

HCID 580029845-(4-Fluorophenyl)-7-isopropyl-6-[4-(trifluoromethoxy)benzoyl]spiro[chromen-2,1'-cyclobutan]-4(3H)-one

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 14798Sodium Hydroxide용매

반응 조건

온도
0 °C

실험 절차

68 mg (0.16 mmol) of 1,1-dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-one are dissolved in 0.6 ml of abs. dichloromethane and cooled to −30° C. 9 μl (0.11 mmol) of pyridine are added, followed by the dropwise addition of 55 mg (0.11 mmol) of 5-(4-fluorophenyl)-6-{hydroxy[4-(trifluoromethoxy)phenyl]methyl}-7-isopropylspiro-[chromen-2,1′-cyclobutan]-4(3H)-one (Example 58A), dissolved in 0.4 ml of abs. dichloromethane. The mixture is slowly warmed to 0° C. and stirred at this temperature for 6 h. The mixture is diluted with ethyl acetate, 5 ml of 1 N aqueous sodium hydroxide solution are added and the mixture is then extracted twice with ethyl acetate. The combined organic phases are washed once with 1 N hydrochloric acid and twice with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The crude product is dried under high vacuum and then reacted without further purification. This gives 54 mg (98% of theory) of the title compound.

후처리

  1. dissolutiondissolved in 0.4 ml of abs
  2. additionare added
  3. extractionthe mixture is then extracted twice with ethyl acetate
  4. washThe combined organic phases are washed once with 1 N hydrochloric acid and twice with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dry with materialThe crude product is dried under high vacuum
  9. customreacted without further purification

출처 및 근거

ORD 기록
ord-be58dda404564a5a95c6a56e664ed471
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227511B2

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