Iodine → 5-(1,3-Dioxan-2-yl)-2-iodo-1-methyl-1H-imidazole

HRID 1942768

反応式

HRID 1942768 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][O:3][CH:2]1[C:7]1[N:11]([CH3:12])[CH:10]=[N:9][CH:8]=1.[Li]CCCC.[I:18]I>C1COCC1>[O:3]1[CH2:4][CH2:5][CH2:6][O:1][CH:2]1[C:7]1[N:11]([CH3:12])[C:10]([I:18])=[N:9][CH:8]=1

参加物

5

反応物 3

HCID 807IodineHCID 579196325-(1,3-Dioxan-2-yl)-1-methyl-1H-imidazoleHCID 178418339Butyllithium

生成物 1

HCID 579195385-(1,3-Dioxan-2-yl)-2-iodo-1-methyl-1H-imidazole収率 59.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of 38 (295 g, 1.754 mmol) in dry THF (10 mL) at −78° C. was added n-BuLi (0.772 mL, 1.929 mmol, 2.5 M solution in hexanes) and the reaction mixture was stirred for 20 min. Iodine (445 mg, 1.754 mmol) in THF (2 mL) was slowly added dropwise while maintaining the temperature at −78° C. and the reaction mixture was stirred for a further 30 min, and was quenched by the addition of water and then extracted with EtOAc. The organic phase was, washed with sodium thiosulfate solution, separated, dried over Na2SO4, filtered and concentrated. Purification by column chromatography (20% EtOAc/Hexane) afforded 39 (305 mg, 59% yield) as a white solid. MS (m/z): 294.1 (M+H).

後処理

  1. stirringthe reaction mixture was stirred for a further 30 min
  2. customwas quenched by the addition of water
  3. extractionextracted with EtOAc
  4. washwashed with sodium thiosulfate solution
  5. customseparated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by column chromatography (20% EtOAc/Hexane)

出典と根拠

ORDレコード
ord-131c2cab4664488e81423e9518a3816e
出典データセット
uspto-grants-2013_03
特許番号
US08389541B2

関連ノート

読み込み中…