Triacetoxyperiodinane → 3,3-dimethyl-4-oxo-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile

HRID 1677524ノート

反応式

HRID 1677524 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH:24]([C:31]1[C:39]2[C:34](=[N:35][CH:36]=[C:37]([C:40]3[CH:45]=[C:44]([O:46][CH3:47])[C:43]([O:48][CH3:49])=[C:42]([O:50][CH3:51])[CH:41]=3)[N:38]=2)[N:33]([Si:52]([CH:59]([CH3:61])[CH3:60])([CH:56]([CH3:58])[CH3:57])[CH:53]([CH3:55])[CH3:54])[CH:32]=1)[C:25]([CH3:30])([CH3:29])[CH2:26][C:27]#[N:28]>ClCCl>[CH3:30][C:25]([CH3:29])([C:24](=[O:23])[C:31]1[C:39]2[C:34](=[N:35][CH:36]=[C:37]([C:40]3[CH:45]=[C:44]([O:46][CH3:47])[C:43]([O:48][CH3:49])=[C:42]([O:50][CH3:51])[CH:41]=3)[N:38]=2)[N:33]([Si:52]([CH:56]([CH3:58])[CH3:57])([CH:53]([CH3:54])[CH3:55])[CH:59]([CH3:61])[CH3:60])[CH:32]=1)[CH2:26][C:27]#[N:28]

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 595407864-hydroxy-3,3-dimethyl-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile

生成物 1

HCID 595409513,3-dimethyl-4-oxo-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile収率 61.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
2.5 °C

実験手順

Dess-Martin periodinane (0.122 g, 0.289 mmol) was added to a 0-5° C. solution of 4-hydroxy-3,3-dimethyl-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile (0.152 g, 0.275 mmol) in 2 mL of dichloromethane. The mixture was stirred at 0-5° C. for 3 h, then quenched with water and a sat. aq. NaHCO3 solution and extracted with 30 mL of dichloromethane. The organic layer was dried over MgSO4, filtered and concentrated to a residue. Column chromatography (0→50% EtOAc/hexanes) afforded 0.093 g (61%) of 3,3-dimethyl-4-oxo-4-[5-triisopropylsilanyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-butyronitrile as a white solid.

後処理

  1. customquenched with water
  2. extractiona sat. aq. NaHCO3 solution and extracted with 30 mL of dichloromethane
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a residue

出典と根拠

ORDレコード
ord-397cc17a29fe485090246bb036375ebc
出典データセット
uspto-grants-2011_08
特許番号
US08008298B2

反応ノート

読み込み中…