Methyl iodide → HCID 67119344, compound

HRID 2076707Notes

Reaction equation

HRID 2076707 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[C:23]([CH3:25])[C:22]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:21][C:20]=2[CH3:31])=[CH:15][CH:14]=1.[CH3:32]I.[Cl-].[NH4+]>O1CCCC1>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[C:23]([CH3:25])[C:22]([CH:26]([CH3:32])[C:27]([O:29][CH3:30])=[O:28])=[CH:21][C:20]=2[CH3:31])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 86241519HCID 86241519, compound

Product 1

HCID 67119344HCID 67119344, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

After a lithium bis(trimethylsilyl)amide 1.0M-tetrahydrofuran solution (3.86 ml, 3.86 mmol) was added to a solution of methyl (4′-methoxy-2,5-dimethyl-1,1′-biphenyl-4-yl)acetate (730 mg, 2.57 mmol) obtained in Example (105-1) in tetrahydrofuran (6 ml) at −78° C., methyl iodide (800 μl, 12.9 mmol) was added dropwise thereto and the mixture was stirred for 1 hour. A saturated aqueous ammonium chloride solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate (twice). 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 column chromatography (eluting solvent: hexane/ethyl acetate=95/5-15/1) to give methyl 2-(4′-methoxy-2,5-dimethyl-1,1′-biphenyl-4-yl)propanoate as a colorless oil (620 mg, 81%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (twice)
  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 column chromatography (eluting solvent: hexane/ethyl acetate=95/5-15/1)

Sources & evidence

ORD record
ord-7bce145f581c44f780973953b2876907
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

Loading…