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Tetrabutylammonium Fluoride → 4-[2-(3-Benzyl-[1,2,4]oxadiazol-5-yl)-vinyl]benzene-1,2-diol

HRID 470608
ノート
印刷プレビュー

反応式

HRID 470608 の反応式
[CH2:1]([C:8]1[N:12]=[C:11]([CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][Si](C(C)(C)C)(C)C)=[C:17]([O:29][Si](C(C)(C)C)(C)C)[CH:16]=2)[O:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([C:8]1[N:12]=[C:11]([CH:13]=[CH:14][C:15]2[CH:16]=[C:17]([OH:29])[C:18]([OH:21])=[CH:19][CH:20]=2)[O:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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 2724141Tetrabutylammonium FluorideHCID 673973153-Benzyl-5-{2-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-vinyl}-[1,2,4]oxadiazole

生成物 1

HCID 1364132114-[2-(3-Benzyl-[1,2,4]oxadiazol-5-yl)-vinyl]benzene-1,2-diol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
5 °C

実験手順

3-Benzyl-5-{2-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-vinyl}-[1,2,4]oxadiazole (compound of Example 4, Method B, Step 1) (4.60 g, 8.79 mmol) was dissolved in THF (30 mL) and cooled to 5° C. This was followed by addition of 1 M solution of TBAF in THF (12.72 mL, 43.95 mL) over a period of 15 min and allowed to warm to room temperature. After 3 h stirring at room temperature, the solvent was evaporated and the reaction mixture was allowed to cool to room temperature. The reaction mixture was diluted with water (30 mL) and stirred for 10 min followed by extraction with ethyl acetate (3×20 mL). The combined organic layers were washed with water (2×10 mL) and brine (10 mL). The organic phase obtained was dried over anhydrous sodium sulfate and concentrated to obtain a crude product, which was purified by column chromatography (silica gel, 0.5% methanol in chloroform) to afford the title compound.

後処理

  1. temperatureto warm to room temperature
  2. customthe solvent was evaporated
  3. temperatureto cool to room temperature
  4. additionThe reaction mixture was diluted with water (30 mL)
  5. stirringstirred for 10 min
  6. extractionfollowed by extraction with ethyl acetate (3×20 mL)
  7. washThe combined organic layers were washed with water (2×10 mL) and brine (10 mL)
  8. customThe organic phase obtained
  9. dry with materialwas dried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. customto obtain a crude product, which
  12. customwas purified by column chromatography (silica gel, 0.5% methanol in chloroform)

出典と根拠

ORDレコード
ord-2dee1e238c644c00b4ba7471cd03ec4e
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08629277B2

反応ノート

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