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

HRID 60652

반응식

HRID 60652 반응식
[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]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 248910Methyl 5-Iodosalicylate

생성물 1

HCID 1233718745-Iodo-2-triisopropylsilanyloxy-benzoic acid methyl ester수율 92.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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+].

후처리

  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

출처 및 근거

ORD 기록
ord-d2b657b18bee487ca61d7522a786f771
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440974B2

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