Ethyl Acetate → HCID 86677561, compound

HRID 1027392Notes

Reaction equation

HRID 1027392 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 (4.5 g, 17.71 mmol) was dissolved in 2-propanol (100 mL) and water (50 mL). To this was added an aqueous solution of NaIO4 (9.5 g, 44.3 mmol) in water (50 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-4cb931df4d8d44c0aea9a8f352e00aae
Source dataset
uspto-grants-2014_05
Patent number
US08735385B2

Reaction notes

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