Methyl 1-allylcyclohexanecarboxylate → Methyl 1-(2-oxoethyl)cyclohexanecarboxylate

HRID 2401089Notes

Reaction equation

HRID 2401089 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:11][CH:12]=C)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].I([O-])(=O)(=O)=[O:15].[Na+]>C(O)(C)C.O.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3]([C:5]1([CH2:11][CH:12]=[O:15])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 2

HCID 10932067Methyl 1-allylcyclohexanecarboxylateHCID 23667635Sodium periodate

Product 1

HCID 23021124Methyl 1-(2-oxoethyl)cyclohexanecarboxylateYield 31%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 3776IsopropanolSolvent2×

Procedure

To a solution of 1-allyl-cyclohexanecarboxylic acid methyl ester (4.0 g, 21.5 mmol) in isopropanol (35 mL) was added a solution of sodium periodate (10.1 g, 47.3 mmol) in H2O (35 mL) followed by the addition of osmium tetroxide (16 mg, 0.065 mmol). More isopropanol (30 mL) and H2O (35 mL) was added and the resulting suspension was stirred for 24 hours. Then, the reaction mixture was poured into ice/H2O (200 mL) and extracted with EtOAc (2×200 mL) in a separatory funnel. The organic layers were combined and dried over Na2SO4, filtered and concentrated to provide a crude oil which was purified by flash column chromatography (10 to 60% EtOAc/heptane) to provide 1.24 g (31% yield over two steps) of the title compound as an oil.

Workup

  1. extractionextracted with EtOAc (2×200 mL) in a separatory funnel
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto provide a crude oil which
  6. customwas purified by flash column chromatography (10 to 60% EtOAc/heptane)

Sources & evidence

ORD record
ord-0f4cef0228734063812fe3a300550095
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

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