Tetrabutylammonium Fluoride → 2-Chloro-5-ethynylpyridine

HRID 2109144노트

반응식

HRID 2109144 반응식
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[C:27][Si](C)(C)C)=[CH:22][N:21]=1>C1COCC1>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[CH:27])=[CH:22][N:21]=1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 106322252-Chloro-5-trimethylsilanylethynyl-pyridine

생성물 1

HCID 106542812-Chloro-5-ethynylpyridine수율 73.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A 1 M solution of TBAF in THF (12 mL) was added to 500 mg (2.38 mmol) of 2-chloro-5-trimethylsilanylethynyl-pyridine and the black solution was stirred overnight. The mixture was concentrated, the resulting residue was stirred in 50 mL of Et2O for 1 h, and the liquid was decanted from the solids. This washing procedure was repeated twice, and the combined washes were concentrated and chromatographed to provide 240 mg of 2-chloro-5-ethynylpyridine as a colorless solid.

후처리

  1. concentrationThe mixture was concentrated
  2. stirringthe resulting residue was stirred in 50 mL of Et2O for 1 h
  3. customthe liquid was decanted from the solids
  4. concentrationthe combined washes were concentrated
  5. customchromatographed

출처 및 근거

ORD 기록
ord-161954b79b5840188d0c17563c7fd872
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07514458B2

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