Sodium Chloride → HCID 67119314, compound

HRID 2076696Notes

Reaction equation

HRID 2076696 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:11]([O:14][C:15]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[C:24]([CH2:32][O:33][C:34]2[CH:39]=[CH:38][C:37]([C:40]3[CH:45]=[CH:44][C:43]([CH2:46][C:47]([O:49][CH3:50])=[O:48])=[CH:42][C:41]=3[CH2:51][CH3:52])=[CH:36][CH:35]=2)[C:16]=1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:12]=[CH2:13].[CH3:53]I.[Na+].[Cl-]>O1CCCC1>[CH2:11]([O:14][C:15]1[C:27]([C:28]([F:30])([F:31])[F:29])=[CH:26][CH:25]=[C:24]([CH2:32][O:33][C:34]2[CH:35]=[CH:36][C:37]([C:40]3[CH:45]=[CH:44][C:43]([CH:46]([C:47]([O:49][CH3:50])=[O:48])[CH3:53])=[CH:42][C:41]=3[CH2:51][CH3:52])=[CH:38][CH:39]=2)[C:16]=1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:12]=[CH2:13]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 67119139HCID 67119139, compound

Product 1

HCID 67119314HCID 67119314, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After lithium bis(trimethylsilyl)amide (1M n-hexane solution, 0.32 ml, 0.32 mmol) was added to a solution of tert-butyl 2-(allyloxy)-6-[({2′-ethyl-4′-[(methoxycarbonyl)methyl]-1,1′-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate (105 mg, 0.19 mmol) in tetrahydrofuran (2 ml) at −78° C. under nitrogen atmosphere and the mixture was stirred for 0.5 hours, methyl iodide (30 μl, 0.48 mmol) was added thereto and the mixture was stirred for 1 hour. After a saturated aqueous NaCl solution was added to the reaction mixture and the mixture was extracted with ethyl acetate, the organic layer was washed with 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: hexane/ethyl acetate=5/1) to give tert-butyl 2-(allyloxy)-6-[({2′-ethyl-4′-[1-(methoxycarbonyl)ethyl]-1,1′-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate as an oil (30 mg, yield: 27%).

Workup

  1. stirringthe mixture was stirred for 1 hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with a saturated aqueous NaCl solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe residue obtained
  6. customby removing the solvent under reduced pressure
  7. customwas purified by silica gel preparative thin layer chromatography (developing solvent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-d79aaa94047e42439c62acce3214f075
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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