Ethyl Acetate → HCID 86677563, compound

HRID 2401094Notes

Reaction equation

HRID 2401094 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:30][CH:31]=C)[CH2:11][CH2:10][CH:9]([O:12][Si:13]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8][CH2:7]1)=[O:5])C.C(OCC)(=[O:35])C>CC(O)C.O.O=[Os](=O)(=O)=O>[CH3:1][O:3][C:4]([C:6]1([CH2:30][CH:31]=[O:35])[CH2:7][CH2:8][CH:9]([O:12][Si:13]([C:26]([CH3:27])([CH3:28])[CH3:29])([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:10][CH2:11]1)=[O:5]

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 67478666HCID 67478666, compound

Product 1

HCID 86677563HCID 86677563, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

1-Allyl-4-(tert-butyl-diphenyl-silanyloxy)-cyclohexanecarboxylic acid ethyl ester (5 g, 11.1 mmol) was dissolved in 2-propanol (100 mL) and water (50 mL). To this was added an aqueous solution of NaIO4 (5.94 g, 27.8 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 at rt. The reaction mixture was poured into ice water (50 mL) and ethyl acetate (EtOAc) (60 mL). The layers were separated and the aqueous layer was extracted with EtOAc (3×50 mL). The combined organic layers 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 4.45 g (87%) of the title compound.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc (3×50 mL)
  3. washThe combined organic layers 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-550a210d6469418aa46850c084d3d436
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

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