Tributyltin Chloride → 2-methyl-1-phenyl-4-tributylstannanyl-1H-imidazole

HRID 1898630노트

반응식

HRID 1898630 반응식
I[C:2]1[N:3]=[C:4]([CH3:13])[N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=1.C([Mg]Cl)(C)C.[CH2:19]([Sn:23](Cl)([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][CH2:21][CH3:22].[NH4+].[Cl-]>C1COCC1.C(OCC)(=O)C>[CH3:13][C:4]1[N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=[C:2]([Sn:23]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:19][CH2:20][CH2:21][CH3:22])[N:3]=1

참가 물질

7

반응물 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 575166484-iodo-2-methyl-1-phenyl-1H-imidazoleHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 575166502-methyl-1-phenyl-4-tributylstannanyl-1H-imidazole수율 23.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

4-Iodo-2-methyl-1-phenyl-1H-imidazole (0.55 g, 1.94 mmol) was dissolved in 9 mL of anhydrous THF and isopropylmagnesium chloride (2 M THF solution, 1.2 mL, 2.4 mmol) was added dropwise. The reaction was stirred for more than 1 h at room temperature. Tributylstannyl chloride (0.55 mL, 2.03 mmol) was slowly added. After the reaction was judged to be complete by TLC, NH4Cl solution and ethyl acetate were added. The layers were separated and the aqueous layer was extracted twice more with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel chromatography (triethylamine/ethyl acetate/hexanes) to give 0.2 g (23%) of 2-methyl-1-phenyl-4-tributylstannanyl-1H-imidazole.

후처리

  1. additionwere added
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted twice more with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (triethylamine/ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-464f3704f7d94c7e8066c5653b6ec4fd
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08518945B2

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