Tetrabutylammonium Fluoride → 2-(4-Fluorobenzoyl)-3-hydroxypyridine

HRID 986975노트

반응식

HRID 986975 반응식
[F:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([C:8]2[C:13]([O:14][Si](CCCC)(CCCC)CCCC)=[CH:12][CH:11]=[CH:10][N:9]=2)=[O:7])=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[F:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([C:8]2[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][N:9]=2)=[O:7])=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 229879642-(4-Fluorobenzoyl)-3-(tributylsilyloxy)pyridine

생성물 1

HCID 229879782-(4-Fluorobenzoyl)-3-hydroxypyridine수율 89.6%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 2-(4-fluorobenzoyl)-3-(tributylsilyloxy)pyridine (3.75 g, 11.3 mmol) in tetrahydrofuran (17 ml) was cooled to 0° C. and tetrabutylammonium fluoride (17 ml, 1.0 M in tetrahydrofuran) was added. After 2 h, the reaction mixture was diluted with ethyl acetate. The organic layer was separated, washed with sodium bicarbonate and brine, and dried over sodium sulfate. The organics were removed in vacuo and the residue was purified on a silica gel column using ethyl acetate-hexane (2:8) as the eluant to give 2-(4-fluorobenzoyl)-3-hydroxypyridine (2.2 g).

후처리

  1. customThe organic layer was separated
  2. washwashed with sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. customThe organics were removed in vacuo
  5. customthe residue was purified on a silica gel column

출처 및 근거

ORD 기록
ord-81604a4f0516495ca88ab980d1cbf15d
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06630485B2

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