Tributyltin Chloride → 5-Tributylstannyl-4-iodo-1-methyl-1H-imidazole

HRID 32605

반응식

HRID 32605 반응식
[I:1][C:2]1[N:3]=[CH:4][N:5]([CH3:8])[C:6]=1I.C([Mg]Br)C.[CH2:13]([Sn:17](Cl)([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16].[NH4+].[Cl-]>C1COCC1.O>[CH2:22]([Sn:17]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:18][CH2:19][CH2:20][CH3:21])[C:6]1[N:5]([CH3:8])[CH:4]=[N:3][C:2]=1[I:1])[CH2:23][CH2:24][CH3:25]

참가 물질

7

반응물 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 3323874,5-Diiodo-1-methyl-1H-imidazoleHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 179657855-Tributylstannyl-4-iodo-1-methyl-1H-imidazole수율 76%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

4,5-Diiodo-1-methyl-1H-imidazole (40.0 g) was stirred in anhydrous THF (560 mL) at ambient temperature and ethylmagnesium bromide (3M in ether, 42.0 mL) was added over 20 minutes under an inert atmosphere. The resulting white precipitate was stirred for 30 minutes then tributyltin chloride (34.2 mL) added dropwise. The resulting clear solution was stirred for 1 hr, then saturated aqueous NH4Cl (50 mL) and water (300 mL) were added. The reaction mixture was extracted with DCM (500 mL), washed with water (3×300 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica eluting with hexane:EtOAc (1:1) to afford the title compound as a colourless oil (45.1 g, 76%);

후처리

  1. stirringThe resulting clear solution was stirred for 1 hr
  2. extractionThe reaction mixture was extracted with DCM (500 mL)
  3. washwashed with water (3×300 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography on silica eluting with hexane:EtOAc (1:1)

출처 및 근거

ORD 기록
ord-863c4d54d6fd4c958f94e004628de8c3
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427616B2

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