Imidazole → 5-Iodo-2-triisopropylsilanyloxy-benzoic acid methyl ester

HRID 60652

反応式

HRID 60652 の反応式
[I:1][C:2]1[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]([OH:12])=[CH:4][CH:3]=1.N1C=CN=C1.Cl[Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21]>CN(C=O)C>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[C:2]([I:1])[CH:3]=[CH:4][C:5]=1[O:12][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21]

参加物

5

反応物 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 248910Methyl 5-Iodosalicylate

生成物 1

HCID 1233718745-Iodo-2-triisopropylsilanyloxy-benzoic acid methyl ester収率 92.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of methyl 5-iodosalicylate (2.00 g, 7.20 mmol) in DMF (20 mL) was treated with imidazole (1.22 g, 18.0 mmol) then chlorotriisopropylsilane (1.85 mL, 8.60 mmol). The mixture was stirred at RT for 18 h. The mixture was evaporated in vacuo and the residue was partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (2×). The combined organic layers were washed with a 10% aqueous citric acid solution, 1N aqueous NaOH solution and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-10% EtOAc in cyclohexane, to give the title compound as a colorless oil (2.88 g, 92%). LCMS (Method 3): Rt 5.72 min, m/z 435 [MH+].

後処理

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was partitioned between EtOAc and water
  3. extractionThe aqueous layer was then extracted with EtOAc (2×)
  4. washThe combined organic layers were washed with a 10% aqueous citric acid solution, 1N aqueous NaOH solution and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by FCC

出典と根拠

ORDレコード
ord-d2b657b18bee487ca61d7522a786f771
出典データセット
uspto-grants-2016_09
特許番号
US09440974B2

関連ノート

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