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

HRID 1017668ノート

反応式

HRID 1017668 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 229879782-(4-Fluorobenzoyl)-3-hydroxypyridine収率 89.6%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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 (17ml, 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).

後処理

  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

出典と根拠

ORDレコード
ord-6790236ef8d44cfea713c2cffb3620e2
出典データセット
uspto-grants-2002_11
特許番号
US06479507B2

反応ノート

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