Potassium Carbonate → HCID 67460430, compound

HRID 554491Notes

Reaction equation

HRID 554491 reaction equation
C([SiH](CC)CC)C.[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH:22]([C:24]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=1)O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][C:24]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 67458542HCID 67458542, compound

Product 1

HCID 67460430HCID 67460430, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a nitrogen stream, triethylsilane (1.84 mL, 11.55 mmol) and a boron trifluoride-diethylether complex (1.33 mL, 10.5 mmol) were added to a solution of (2-benzyloxyphenyl)-(4-bromophenyl)methanol (3.88 g, 10.5 mmol) in acetonitrile (19.5 mL) at −40° C. and the mixture was stirred at the same temperature for 0.5 hour. A saturated potassium carbonate aqueous solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:10)] to obtain the title compound (2.86 g, 77%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. distillationthe solvent was distilled under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:10)]

Sources & evidence

ORD record
ord-162a80cbc0064e4d9aabff71ed9982fd
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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