Bromotrimethylsilane → Tert-butyl 2-hydroxy-3-methoxy-6-[({4'-[(methoxycarbonyl)methyl]-1,1'-biphenyl-4-yl}oxy)methyl]benzoate

HRID 2076664Notes

Reaction equation

HRID 2076664 reaction equation
C[Si](Br)(C)C.[CH3:6][O:7][C:8]1[C:9]([O:40]COC)=[C:10]([C:18]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][C:32]([CH2:35][C:36]([O:38][CH3:39])=[O:37])=[CH:31][CH:30]=3)=[CH:25][CH:24]=2)=[CH:19][CH:20]=1)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(=O)([O-])O.[Na+]>ClCCl>[OH:40][C:9]1[C:8]([O:7][CH3:6])=[CH:20][CH:19]=[C:18]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]3[CH:34]=[CH:33][C:32]([CH2:35][C:36]([O:38][CH3:39])=[O:37])=[CH:31][CH:30]=3)=[CH:25][CH:24]=2)[C:10]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 76113BromotrimethylsilaneHCID 516892Sodium BicarbonateHCID 67119264Tert-butyl 3-methoxy-2-(methoxymethoxy)-6-[({4'-[(methoxycarbonyl)methyl]-1,1'-biphenyl-4-yl}oxy)methyl]benzoate

Product 1

HCID 67119100Tert-butyl 2-hydroxy-3-methoxy-6-[({4'-[(methoxycarbonyl)methyl]-1,1'-biphenyl-4-yl}oxy)methyl]benzoateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After trimethylsilyl bromide (55 μl, 0.414 mmol) was added to a solution of tert-butyl 3-methoxy-2-(methoxymethoxy)-6-[({4′-[(methoxycarbonyl)methyl]-1,1′-biphenyl-4-yl}oxy)methyl]benzoate (180 mg, 0.344 mmol) obtained in Example (51-1) in dichloromethane (4.0 ml), the mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into an aqueous sodium hydrogencarbonate solution and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel preparative thin layer chromatography (developing solvent: n-hexane/ethyl acetate=2/1) to give tert-butyl 2-hydroxy-3-methoxy-6-[({4′-[(methoxycarbonyl)methyl]-1,1′-biphenyl-4-yl}oxy)methyl]benzoate (146 mg, yield: 89%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was successively washed with water
  3. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  4. customThe residue obtained
  5. customby removing the solvent under reduced pressure
  6. customwas purified by silica gel preparative thin layer chromatography (developing solvent: n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-b459fe6803c3492ab0a6f2d40566aaa1
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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