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Triacetoxyperiodinane → (5-Phenylisoxazol-3-yl)(3,4,5-trimethoxyphenyl)methanone

HRID 70024
ノート
印刷プレビュー

反応式

HRID 70024 の反応式
[C:1]1([C:7]2[O:11][N:10]=[C:9]([CH:12]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)[OH:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 53364193(5-Phenylisoxazol-3-yl)(3,4,5-trimethoxyphenyl)methanol

生成物 1

HCID 53364127(5-Phenylisoxazol-3-yl)(3,4,5-trimethoxyphenyl)methanone収率 70.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 40i (0.110 g, 0.73 mmoL) in 8 mL anhydrous CH2Cl2 was added Dess-Martin reagent (0.274 g, 0.645 mmol). The mixture was allowed to stir for 30 min and quenched with sat. Na2S2O3 solution, extracted with ethyl acetate and dried with MgSO4. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography to give pure compound 1i (70.1%). NMR (CDCl3) δ 7.87-7.85 (m, 2H); 7.72 (s, 2H), 7.53-7.49 (m, 3H), 7.05 (s, 1H), 7.82 (d, 1H, J=1.5 Hz), 3.97 (s, 3H), 3.96 (s, 6H); MS (ESI) m/z 362.1 (M+H)+.

後処理

  1. customquenched with sat. Na2S2O3 solution
  2. extractionextracted with ethyl acetate
  3. dry with materialdried with MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customto yield a crude product, which
  6. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-a70f0bf9c80d41c098d56675f32214ab
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822513B2

反応ノート

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