Ethyl Acetate → HCID 86677561, compound

HRID 2401087Notes

Reaction equation

HRID 2401087 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:15][CH:16]=C)[CH2:10][CH2:9][CH:8]([C:11]([O:13][CH3:14])=[O:12])[CH2:7][CH2:6]1)=[O:4].C(OCC)(=[O:20])C>CC(O)C.O.O=[Os](=O)(=O)=O>[CH3:1][O:2][C:3]([C:5]1([CH2:15][CH:16]=[O:20])[CH2:6][CH2:7][CH:8]([C:11]([O:13][CH3:14])=[O:12])[CH2:9][CH2:10]1)=[O:4]

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 67478669HCID 67478669, compound

Product 1

HCID 86677561HCID 86677561, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

1-Allyl-cyclohexane-1,4-dicarboxylic acid dimethyl ester (4.50 g, 17.71 mmol) was dissolved in 2-propanol (100.0 mL) and water (50.0 mL). To this was added an aqueous solution of NaIO4 (9.50 g, 44.3 mmol) in water (50.0 mL), followed by addition of OsO4 (0.025 g, crystals, in one portion). The reaction mixture was allowed to stir for 16 hours. Then, the reaction mixture was poured into ice water (50 mL) and ethyl acetate (EtOAc) (60 mL). The two layers were separated and the aqueous layer was extracted with EtOAc (3×50 mL). The combined organic solutions were washed with brine, and concentrated to dryness. The material was then purified over silica gel column eluting with ethyl acetate in heptanes (0-60%) to afford 3.09 g (72%) of the title compound.

Workup

  1. customThe two layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc (3×50 mL)
  3. washThe combined organic solutions were washed with brine
  4. concentrationconcentrated to dryness
  5. customThe material was then purified over silica gel column
  6. washeluting with ethyl acetate in heptanes (0-60%)

Sources & evidence

ORD record
ord-6130df2f6fda40298822a83cb6d948f9
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

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