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

HRID 1942768

반응식

HRID 1942768 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-131c2cab4664488e81423e9518a3816e
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389541B2

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