Sodium Cyanide → [4-(1,3-Benzoxazol-2-yl)-2-hydroxyphenyl]acetonitrile

HRID 7707

反応式

HRID 7707 の反応式
C([Si](C)(C)[O:6][C:7]1[CH:8]=[C:9]([C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH:10]=[CH:11][C:12]=1[CH2:13]Br)(C)(C)C.[C-:26]#[N:27].[Na+]>CN(C=O)C.CCOC(C)=O>[O:16]1[C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=[C:15]1[C:9]1[CH:10]=[CH:11][C:12]([CH2:13][C:26]#[N:27])=[C:7]([OH:6])[CH:8]=1

参加物

5

反応物 2

HCID 8929Sodium CyanideHCID 695845532-(3-{[Tert-butyl-(dimethyl)silyl]oxy}-4-bromomethylphenyl)-1,3-benzoxazole

生成物 1

HCID 10149217[4-(1,3-Benzoxazol-2-yl)-2-hydroxyphenyl]acetonitrile

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

The mixture of 2-(3-{[tert-butyl-(dimethyl)silyl]oxy}-4-bromomethylphenyl)-1,3-benzoxazole (1.6 g, 3.8 mmol) and sodium cyanide (560 mg, 11.4 mmol) in DMF (10 mL) was stirred at 90° C. overnight. After cooling to rt, the mixture was diluted with EtOAc (100 mL), washed with H2O (2×50 mL), dried (MgSO4), filtered, and concentrated in vacuo to afford the desired [4-(1,3-benzoxazol-2-yl)-2-hydroxyphenyl]acetonitrile as yellow solid. 1H NMR(CD3OD, 300 MHz), δ10.6(s, 1H), 7.8(m, 2H), 7.7(m, 2H), 7.5(d, 1H), 7.4(m, 2H). MS (ESI) 251 (M+H)+.

後処理

  1. temperatureAfter cooling to rt
  2. washwashed with H2O (2×50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4c0144b583b2473bbec649c275f7dd30
出典データセット
uspto-grants-2006_08
特許番号
US07087601B2

関連ノート

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