Water → HCID 67119298, compound

HRID 2076706Notes

Reaction equation

HRID 2076706 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][C:36]([CH:39]([CH3:44])[C:40]([O:42][CH3:43])=[O:41])=[C:35]([CH2:45][CH3:46])[CH:34]=2)=[CH:29][CH:28]=1)(C(C)(C)C)(C)C.O>O1CCCC1>[CH2:45]([C:35]1[CH:34]=[C:33]([C:30]2[CH:31]=[CH:32][C:27]([OH:26])=[CH:28][CH:29]=2)[CH:38]=[CH:37][C:36]=1[CH:39]([CH3:44])[C:40]([O:42][CH3:43])=[O:41])[CH3:46]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 67119136HCID 67119136, compound

Product 1

HCID 67119298HCID 67119298, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A tetra-n-butylammonium fluoride-11.0M tetrahydrofuran solution (0.39 ml, 0.391 mmol) was added to a solution of methyl 2-(4′-{[tert-butyl(dimethyl)silyl]oxy}-3-ethyl-1,1′-biphenyl-4-yl)propionate (104 mg, 283 mmol) obtained in Example (103-1) in tetrahydrofuran (5 ml), and the mixture was stirred at room temperature for 1.5 hours. After water 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 column chromatography (developing solvent: hexane/ethyl acetate=3/1) to give methyl 2-(3-ethyl-4′-hydroxy-1,1′-biphenyl-4-yl)propionate (76 mg, 1009).

Workup

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

Sources & evidence

ORD record
ord-20b023c30aaf4b04b618f94aad018f8d
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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