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

HRID 1516724ノート

反応式

HRID 1516724 の反応式
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

参加物

7

反応物 4

HCID 1049PyridineHCID 6344Dichloromethane2 回HCID 159087TriacetoxyperiodinaneHCID 580029385-(4-Fluorophenyl)-6-{hydroxy[4-(trifluoromethoxy)phenyl]methyl}-7-isopropylspiro[chromen-2,1'-cyclobutan]-4(3H)-one

生成物 1

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

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-be58dda404564a5a95c6a56e664ed471
出典データセット
uspto-grants-2012_07
特許番号
US08227511B2

反応ノート

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