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

HRID 7694

반응식

HRID 7694 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-26845d3d550d49b5a8a35ee75d6d3a4d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087601B2

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