Tetrabutylammonium Fluoride → 5-(Cyclopropylmethoxy)-2-ethynylpyridine

HRID 1026315ノート

反応式

HRID 1026315 の反応式
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]([C:12]#[C:13][Si](C)(C)C)=[N:10][CH:11]=2)[CH2:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]([C:12]#[CH:13])=[N:10][CH:11]=2)[CH2:2][CH2:3]1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 677778225-(Cyclopropylmethoxy)-2-[(trimethylsilyl)ethynyl]pyridine

生成物 1

HCID 580470405-(Cyclopropylmethoxy)-2-ethynylpyridine収率 108.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 5-(cyclopropylmethoxy)-2-[(trimethylsilyl)ethynyl]pyridine (773 mg) in THF (15 mL) was added a THF solution (1.0 M, 4.1 mL) of tetrabutylammonium fluoride at room temperature, and the reaction mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate and water, and the aqueous layer was separated from the organic layer. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a colorless oil (591 mg).

後処理

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with ethyl acetate and water
  3. customthe aqueous layer was separated from the organic layer
  4. extractionThe separated aqueous layer was extracted again with ethyl acetate
  5. washThe combined organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-117be9943f804f5f9e5adf491693a5e3
出典データセット
uspto-grants-2014_05
特許番号
US08729102B2

反応ノート

読み込み中…