Trimethylsilyl cyanide → [4-(1,3-Benzoxazol-2-yl)-2-(trifluoromethyl)phenyl]acetonitrile

HRID 7694

反応式

HRID 7694 の反応式
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][C:4]=1[C:18]([F:21])([F:20])[F:19].[C:22]([Si](C)(C)C)#[N:23].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C(#N)C>[O:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:9]1[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:22]#[N:23])=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:5]=1

参加物

5

反応物 3

HCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 219909772-[4-(Bromomethyl)-3-(trifluoromethyl)phenyl]-1,3-benzoxazole

生成物 1

HCID 10125560[4-(1,3-Benzoxazol-2-yl)-2-(trifluoromethyl)phenyl]acetonitrile

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a suspension of 2-[4-(bromomethyl)-3-(trifluoromethyl)phenyl]-1,3-benzoxazole (528 mg, 1.5 mmol) and cyanotrimethylsilane (0.30 mL, 2.2 mmol) in acetonitrile (19 mL) was added TBAF (1.0M in THF, 2.2 mL, 2.2 mmol) and the mixture was stirred at rt for 2 h. The solvent was removed in vacuo and the crude was purified by flash chromatography eluting with EtOAc:hexanes (1:9) to afford the desired [4-(1,3-benzoxazol-2-yl)-2-(trifluoromethyl)phenyl]acetonitrile as a colorless solid. 1H NMR (CDCl3, 300 MHz) δ 8.60 (s, 1H), 8.48 (d, 1H), 7.88 (d, 1H), 7.82 (m, 1H), 7.63 (m, 1H), 7.43 (m, 2H), 4.05 (s, 2H). MS (ESI) 303 (M+H)+.

後処理

  1. customThe solvent was removed in vacuo
  2. customthe crude was purified by flash chromatography
  3. washeluting with EtOAc:hexanes (1:9)

出典と根拠

ORDレコード
ord-26845d3d550d49b5a8a35ee75d6d3a4d
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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