Imidazole → HCID 131734519, compound

HRID 591412Notes

Reaction equation

HRID 591412 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:9]2[C:10]([OH:15])=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[S:7][CH:6]=1.CN(C=O)C.N1C=CN=C1.[CH:27]([Si:30](Cl)([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])([CH3:29])[CH3:28]>O>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:9]2[C:10]([OH:15])=[CH:11][C:12]([O:14][Si:30]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:27]([CH3:29])[CH3:28])=[CH:13][C:8]=2[S:7][CH:6]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 139400Triisopropylsilyl chlorideHCID 121223266HCID 121223266, compound

Product 1

HCID 131734519HCID 131734519, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl(4,6-dihydroxy-1-benzothiophen-3-yl)acetate (7.7 g) and DMF (dry) (150 mL) was added imidazole (4.40 g) at room temperature, and the mixture was added slowly triisopropylsilyl chloride (7.61 mL) over a period of 20 min, and the mixture was stirred at room temperature for 48 h. The mixture was poured into water at room temperature and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (8.10 g).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-d10994e4f06e4a0b94a20446a1d772e3
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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