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Potassium tert-butoxide → HCID 178437374、化合物

HRID 925930
ノート
印刷プレビュー

反応式

HRID 925930 の反応式
[C:1]([C:4]1[C:9]([NH:10][C:11]([C:13]2[S:14][CH:15]=[C:16]([C:18]#[C:19][Si](C)(C)C)[N:17]=2)=O)=[C:8]([CH3:24])[C:7]([O:25][CH3:26])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CC(C)([O-])C.[K+]>C(O)(C)(C)C>[CH3:26][O:25][C:7]1[C:8]([CH3:24])=[C:9]2[C:4]([C:1]([OH:3])=[CH:2][C:11]([C:13]3[S:14][CH:15]=[C:16]([C:18]#[CH:19])[N:17]=3)=[N:10]2)=[CH:5][CH:6]=1
参加物反応条件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 23665647Potassium tert-butoxideHCID 672140214-Trimethylsilanylethynyl-thiazole-2-carboxylic acid-(6-acetyl-3-methoxy-2-methyl-phenyl)-amide

生成物 1

HCID 178437374HCID 178437374、化合物収率 52%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

反応条件

温度
80 °C

実験手順

To a suspension of compound 208b (8.71 g, 1 eq.) in tert-butanol (240 mL) was added potassium tert-butoxide (5.32 g, 2.1 eq.). The heterogeneous mixture was stirred and heated to 80° C. The solvent was then evaporated and water was added to the resulting black residue. The pH of the mixture was brought to 6 with 1N HCl. The mixture was extracted with dichloromethane. The organic layer was dried over Na2SO4, filtered, and concentrated under vacuo. The solid was purified by chromatography on silica gel to give compound 209b as an orange solid in 52% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 2.45 (s, 3H), 3.25 (s, 1H), 3.99 (s, 3H), 6.89 (br s, 1H), 7.06 (d, J=9.09 Hz, 1H), 7.72 (s, 1H), 8.26 (d, J=9.09 Hz, 1H), 9.50 (br s, 1H); MS (ESI, EI+): m/z=297 (MH+).

後処理

  1. customThe solvent was then evaporated
  2. additionwater was added to the resulting black residue
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuo
  7. customThe solid was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-ed1742d2fbae426f99103fe32eb661ac
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09284307B2

反応ノート

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