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Triacetoxyperiodinane → 6-(4-tert-butylbenzoyl)-5-(4-fluorophenyl)-7-isopropyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one

HRID 1516702
ノート
印刷プレビュー

反応式

HRID 1516702 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[C:23]([C:27]1[CH:32]=[CH:31][C:30]([CH:33]([OH:57])[C:34]2[C:35]([C:50]3[CH:55]=[CH:54][C:53]([F:56])=[CH:52][CH:51]=3)=[C:36]3[C:41](=[CH:42][C:43]=2[CH:44]([CH3:46])[CH3:45])[O:40][C:39]([CH3:48])([CH3:47])[CH2:38][C:37]3=[O:49])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24].C(C1C=CC(C(O)C2C(C3C=CC(F)=CC=3)=C3C(=CC=2CCC)OC(C)(C)CC3=O)=CC=1)(C)(C)C>ClCCl>[C:23]([C:27]1[CH:28]=[CH:29][C:30]([C:33]([C:34]2[C:35]([C:50]3[CH:51]=[CH:52][C:53]([F:56])=[CH:54][CH:55]=3)=[C:36]3[C:41](=[CH:42][C:43]=2[CH:44]([CH3:46])[CH3:45])[O:40][C:39]([CH3:47])([CH3:48])[CH2:38][C:37]3=[O:49])=[O:57])=[CH:31][CH:32]=1)([CH3:25])([CH3:26])[CH3:24]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 159087TriacetoxyperiodinaneHCID 58002954Rac-6-[(4-tert-butylphenyl)(hydroxy)methyl]-5-(4-fluorophenyl)-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-oneHCID 69070315Rac-6-[(4-tert-butylphenyl)(hydroxy)methyl]-5-(4-fluorophenyl)-7-n-propyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one

生成物 1

HCID 580030386-(4-tert-butylbenzoyl)-5-(4-fluorophenyl)-7-isopropyl-2,2-dimethyl-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., 340 mg (800 μmol) of 1,1-dihydro-1,1,1-triacetoxy-1,2-benziodoxol-3(1H)-one are added to a solution of 190 mg (400 μmol) of a 2:1 mixture of rac-6-[(4-tert-butylphenyl)(hydroxy)-methyl]-5-(4-fluorophenyl)-7-isopropyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (Example 27A) and rac-6-[(4-tert-butylphenyl)(hydroxy)methyl]-5-(4-fluorophenyl)-7-n-propyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one in 7.5 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 preparative HPLC (method 1) and subsequent column chromatography on silica gel (mobile phase: gradient cyclohexane→cyclohexane/dichloromethane/ethyl acetate 20:20:0.5).

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 preparative HPLC (method 1) and subsequent column chromatography on silica gel (mobile phase: gradient cyclohexane→cyclohexane/dichloromethane/ethyl acetate 20:20:0.5)

出典と根拠

ORDレコード
ord-326b956726f54ad9946c6f7e9eb0991f
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08227511B2

反応ノート

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