Triacetoxyperiodinane → 5-(4-fluorophenyl)-7-isopropyl-2,2-dimethyl-6-[4-(trifluoromethyl)benzoyl]-2,3-dihydro-4H-chromen-4-one

HRID 1516696ノート

反応式

HRID 1516696 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[C:39]([CH:40]([OH:51])[C:41]3[CH:46]=[CH:45][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:43][CH:42]=3)=[C:38]([CH:52]([CH3:54])[CH3:53])[CH:37]=[C:36]3[C:31]=2[C:32](=[O:57])[CH2:33][C:34]([CH3:56])([CH3:55])[O:35]3)=[CH:26][CH:25]=1>ClCCl>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[C:39]([C:40](=[O:51])[C:41]3[CH:46]=[CH:45][C:44]([C:47]([F:49])([F:50])[F:48])=[CH:43][CH:42]=3)=[C:38]([CH:52]([CH3:53])[CH3:54])[CH:37]=[C:36]3[C:31]=2[C:32](=[O:57])[CH2:33][C:34]([CH3:55])([CH3:56])[O:35]3)=[CH:26][CH:25]=1

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 69070570Rac-5-(4-fluorophenyl)-6-{hydroxy[4-(trifluoromethyl)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one

生成物 1

HCID 580029755-(4-fluorophenyl)-7-isopropyl-2,2-dimethyl-6-[4-(trifluoromethyl)benzoyl]-2,3-dihydro-4H-chromen-4-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

At 0° C., 174 mg (410 μmol) of 1,1-dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-one are added to a solution of 100 mg (207 μmol) of rac-5-(4-fluorophenyl)-6-{hydroxy[4-(trifluoromethyl)-phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (Example 21A) in 4.5 ml of dichloromethane, and the mixture is stirred at this temperature for 4 h. The mixture is then diluted with dichloromethane and washed three times with 1 M aqueous sodium hydroxide solution. The organic phase is dried over magnesium sulfate and then concentrated under reduced pressure, and the residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 20:1).

後処理

  1. washwashed three times with 1 M aqueous sodium hydroxide solution
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe residue is purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 20:1)

出典と根拠

ORDレコード
ord-a660f838fa204cc88c155e92b59a7288
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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