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

HRID 1898630ノート

反応式

HRID 1898630 の反応式
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

参加物

7

反応物 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 575166484-iodo-2-methyl-1-phenyl-1H-imidazoleHCID 178418918HCID 178418918、化合物

生成物 1

HCID 575166502-methyl-1-phenyl-4-tributylstannanyl-1H-imidazole収率 23.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-464f3704f7d94c7e8066c5653b6ec4fd
出典データセット
uspto-grants-2013_08
特許番号
US08518945B2

反応ノート

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