Imidazole → tert-Butyl(4-chloro-3-iodophenoxy)dimethylsilane

HRID 1846033ノート

反応式

HRID 1846033 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[I:9].[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1.CCOC(C)=O>CC1CCCO1>[C:13]([Si:10]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([I:9])[CH:4]=1)([CH3:12])[CH3:11])([CH3:16])([CH3:15])[CH3:14]

参加物

6

反応物 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 229287294-Chloro-3-iodophenol

生成物 1

HCID 86723256tert-Butyl(4-chloro-3-iodophenoxy)dimethylsilane収率 30%

試薬・触媒・溶媒 1

HCID 73012-Methyltetrahydrofuran溶媒

実験手順

To a solution of 4-chloro-3-iodophenol (2 g. 7.86 mmol) in anhydrous 2-methyltetrahydrofuran (10 mL) was added tert-butyldimethylsilyl chloride (1.25 g, 8.28 mmol) followed by imidazole (642 mg, 68.1 mmol) The resulting mixture was stirred at room temperature for 3 hours. EtOAc (10 mL) was added and the mixture washed with aqueous sodium hydroxide solution (2M, 3×10 mL), water (10 mL), and brine (10 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with heptane:EtOAc 90:10 to afford the title compound as colourless oil in 30% yield, 870 mg.

後処理

  1. washthe mixture washed with aqueous sodium hydroxide solution (2M, 3×10 mL), water (10 mL), and brine (10 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography
  5. washeluting with heptane:EtOAc 90:10

出典と根拠

ORDレコード
ord-36c66526bb2746d2a044d3adb874ff5b
出典データセット
uspto-grants-2015_02
特許番号
US08952008B2

反応ノート

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