Tetrabutylammonium Fluoride → 5-(4-Chlorophenyl)-2-ethynyl-3-fluoropyridine

HRID 734800ノート

反応式

HRID 734800 の反応式
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([C:26]#[C:27][C:28]1[C:33]([F:34])=[CH:32][C:31]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)=[CH:30][N:29]=1)(C(C)(C)C)(C)C>C(Cl)Cl>[Cl:41][C:38]1[CH:39]=[CH:40][C:35]([C:31]2[CH:32]=[C:33]([F:34])[C:28]([C:27]#[CH:26])=[N:29][CH:30]=2)=[CH:36][CH:37]=1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 690583282-[(Tert-butyldimethylsilanyl)ethynyl]-5-(4-chlorophenyl)-3-fluoropyridine

生成物 1

HCID 600554165-(4-Chlorophenyl)-2-ethynyl-3-fluoropyridine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1.14 g (3.61 mmol) of TBAF was added at RT to a solution of 1.25 g (3.61 mmol) of 2-[(tert-butyldimethylsilanyl)ethynyl]-5-(4-chlorophenyl)-3-fluoropyridine in 30 mL of DCM and the mixture was stirred for 2 hours. The organic phase was washed with water, dried over sodium sulfate, and evaporated down in vacuo. The residue was stirred with PE, the precipitate was filtered off, washed with PE, and dried in the air. Yield: 0.72 g (86% of theoretical); C13H7ClFN (M=231.653); calc.: molpeak (M+H)+: 232/234 (Cl); found: molpeak (M+H)+: 232/234 (Cl); HPLC-MS: 5.81 minutes (method B).

後処理

  1. washThe organic phase was washed with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated down in vacuo
  4. stirringThe residue was stirred with PE
  5. filtrationthe precipitate was filtered off
  6. washwashed with PE
  7. customdried in the air
  8. custom5.81 minutes (method B)

出典と根拠

ORDレコード
ord-edf9bac4da0745ca9fd47e96455dba3f
出典データセット
uspto-grants-2009_09
特許番号
US07592358B2

反応ノート

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