Pinacol → HCID 11264169, compound

HRID 1791033Notes

Reaction equation

HRID 1791033 reaction equation
C=[C:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[C:10]([CH:13]([OH:15])[CH3:14])[CH:11]=[CH:12][C:5]=2[O:4][CH2:3]1.[OH:16]C(C(O)(C)C)(C)C.I([O-])(=O)(=O)=O.[Na+].C(Cl)(Cl)(Cl)Cl.C(#N)C.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>O.O.O.[Ru](Cl)(Cl)Cl.ClCCl>[C:13]([C:10]1[CH:11]=[CH:12][C:5]2[O:4][CH2:3][C:2](=[O:16])[CH2:8][CH2:7][C:6]=2[CH:9]=1)(=[O:15])[CH3:14]

Participants

8

Reactant 5

HCID 6425PinacolHCID 24477Sodium ThiosulfateHCID 11206499HCID 11206499, compoundHCID 22592919water acetonitrile CCl4HCID 23667635Sodium periodate

Product 1

HCID 11264169HCID 11264169, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 12090026Ruthenium chloride trihydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

4.7 mg (0.023 mmol) of ruthenium chloride trihydrate are added at 0° C. to 188 mg of 1-(3-methylene-2,3,4,5-tetrahydro-1-benzoxepin-7-yl)ethanol as a mixture with its pinacol dimer, prepared according to example 15, and 1.28 g (5.99 mmol) of sodium periodate in solution in a carbon tetrachloride/acetonitrile/water (2/2/3) ternary mixture. After stirring at ambient temperature for 24 hours, a saturated sodium thiosulfate solution and dichloromethane are added. After separating the phases, the aqueous phase is extracted 3 times with dichloromethane. The combined organic phases are washed with brine, are then dried and are finally concentrated under vacuum. Rapid filtration through silica gel (ethyl acetate/heptane 30/70) provides 87 mg (55%) of 7-acetyl-4,5-dihydro-1-benzoxepin-3(2H)-one in the form of a white solid; M.p.=80–82° C.

Workup

  1. customprepared
  2. customAfter separating the phases
  3. extractionthe aqueous phase is extracted 3 times with dichloromethane
  4. washThe combined organic phases are washed with brine
  5. customare then dried
  6. concentrationare finally concentrated under vacuum
  7. filtrationRapid filtration through silica gel (ethyl acetate/heptane 30/70)

Sources & evidence

ORD record
ord-f249fafa738e4090a7c960870da6049d
Source dataset
uspto-grants-2006_07
Patent number
US07071340B2

Reaction notes

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