Methyl iodide → HCID 67119122, compound

HRID 2076702Notes

Reaction equation

HRID 2076702 reaction equation
[OH-].[Na+].[CH3:3]I.[CH2:5]([O:8][C:9]1[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[C:18]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:39]=[CH:38][C:37]([CH2:40][C:41]([O:43][CH2:44][CH:45]=[CH2:46])=[O:42])=[C:36]([Cl:47])[CH:35]=3)=[CH:30][CH:29]=2)[C:10]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH2:7]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH2:5]([O:8][C:9]1[C:21]([C:22]([F:24])([F:25])[F:23])=[CH:20][CH:19]=[C:18]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:39]=[CH:38][C:37]([CH:40]([C:41]([O:43][CH2:44][CH:45]=[CH2:46])=[O:42])[CH3:3])=[C:36]([Cl:47])[CH:35]=3)=[CH:30][CH:29]=2)[C:10]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH2:7]

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 14798Sodium Hydroxide2×HCID 67119197HCID 67119197, compound

Product 1

HCID 67119122HCID 67119122, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

tetra-n-Butylammonium hydrogensulfate (21 mg, 0.062 mmol), a 2N aqueous sodium hydroxide solution (0.06 ml, 0.12 mmol) and methyl iodide (10 μl, 0.16 mmol) were added to a solution of tert-butyl 2-(allyloxy)-6-{[(4′-{[(allyloxy)carbonyl]methyl}-3′-chloro-1,1′-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoate (19 mg, 0.03 mmol) obtained in Example (18-3) in dichloromethane (0.4 ml), and the mixture was stirred at room temperature for 1.5 hours. A 2N aqueous sodium hydroxide solution (0.03 ml, 0.06 mmol) and methyl iodide (7 μl, 0.11 mmol) were added to the reaction mixture and the mixture was further stirred for 1 hour. The residue obtained by removing the solvent under reduced pressure was purified by silica gel preparative thin layer chromatography (developing solvent: hexane/ethyl acetate=5/1) to give tert-butyl 2-(allyloxy)-6-{[(4′-{1-[(allyloxy)carbonyl]ethyl}-3′-chloro-1,1′-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoate (8 mg, yield: 42%).

Workup

  1. stirringthe mixture was further stirred for 1 hour
  2. customThe residue obtained
  3. customby removing the solvent under reduced pressure
  4. customwas purified by silica gel preparative thin layer chromatography (developing solvent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-ad414a2a24014f2c9d507838434a0ab9
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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