Water → (3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-yl)-methanol

HRID 402375ノート

反応式

HRID 402375 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[N:10][N:9]([CH2:12][Si](C)(C)C)[C:8]=1[CH2:17][OH:18].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:12][N:9]1[C:8]([CH2:17][OH:18])=[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[N:11]=[N:10]1

参加物

5

反応物 3

HCID 962Water2 回HCID 2724141Tetrabutylammonium FluorideHCID 67498211(5-pyridin-2-yl-3-trimethylsilanylmethyl-3H-[1,2,3]triazol-4-yl)-methanol

生成物 1

HCID 67498007(3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-yl)-methanol収率 61%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of (5-pyridin-2-yl-3-trimethylsilanylmethyl-3H-[1,2,3]triazol-4-yl)-methanol (364 mg, 1.39 mmol) in THF (23 mL) was added water (50 μL, 2.78 mmol) and then tetrabutylammonium fluoride (1 M in THF, 1.66 mL, 1.66 mmol) added dropwise at 0° C. The reaction mixture was stirred at 0° C. for 15 min. The resulting mixture was poured into water and then the THF was evaporated. The aqueous layer was then extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 100% ethyl acetate in heptane) afforded the title compound (161 mg, 61%) as an off white solid. MS: m/e=191.2 [M+H]+.

後処理

  1. customthe THF was evaporated
  2. extractionThe aqueous layer was then extracted with ethyl acetate
  3. washthe combined organic extracts washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by chromatography (silica, 0 to 100% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-63322169809242d18228438fd3c31062
出典データセット
uspto-grants-2014_06
特許番号
US08742097B2

反応ノート

読み込み中…