Water → 15-Methyl-1-oxacycloheptadecane-2,13-dione

HRID 355542Notes

Reaction equation

HRID 355542 reaction equation
[OH2:1].I([O-])(=O)(=O)=O.[Na+].[CH3:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH2:14]([O:16][C:17](=[O:19])[CH3:18])[CH3:15].ClCCl.[C:23](#N)[CH3:24]>C(Cl)(Cl)(Cl)Cl.O.[Ru](Cl)(Cl)Cl>[CH3:8][CH:9]1[CH2:15][CH2:14][O:16][C:17](=[O:19])[CH2:18][CH2:24][CH2:23][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:13][CH2:12][C:11](=[O:1])[CH2:10]1

Participants

8

Reactant 5

HCID 962Water2×HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 21226206Ethyl acetate hexaneHCID 23667635Sodium periodate

Product 1

HCID 1894286315-Methyl-1-oxacycloheptadecane-2,13-dione

Reagents, catalysts & solvents 2

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To the enol ether (2.10 g, 8.4 mmol) in CCl4 (20 ml), acetonitrile (20 ml), and water (30 ml) at room temperature was added sodium metaperiodate (6.75 g, 35.3 mmol) followed by ruthenium chloride hydrate (50 mg). The mixture was stirred vigourously and an exotherm was noted (approx 5° C.). Once the exotherm had subsided the dark/opaque solution was checked with TLC (9:1, hexane/ethylacetate) which showed the reaction to be complete after 15 minutes. To the reaction mixture was added a 1:1 mixture of dichloromethane and water (60 ml). The organic fractions were separated and dried and the solvent evaporated under reduced pressure to yield a dark oil. The oil was purified by column chromatography, eluting the product with 10% diethyl ether in pentane. The product is a colourless to pale yellow oil. Yield is 1.64 g (69%).

Workup

  1. custom(approx 5° C.)
  2. customthe reaction
  3. additionTo the reaction mixture was added
  4. customThe organic fractions were separated
  5. customdried
  6. customthe solvent evaporated under reduced pressure
  7. customto yield a dark oil
  8. customThe oil was purified by column chromatography
  9. washeluting the product with 10% diethyl ether in pentane

Sources & evidence

ORD record
ord-3aca9acec3414cb492b291cd5dc42cc3
Source dataset
uspto-grants-1998_11
Patent number
US05831101

Reaction notes

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