Hydrogen Peroxide → HCID 66640067, compound

HRID 1094487Notes

Reaction equation

HRID 1094487 reaction equation
[CH:1]1CCCCC=1.[CH3:7][O:8][C:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][C:12]=1C#C[Si](C)(C)C)=[O:10].[C:27]([O-:30])(O)=[O:28].[Na+].OO>C1COCC1>[CH3:7][O:8][C:9]([C:11]1[C:20]2[C:15](=[CH:16][C:17]([CH2:1][C:27]([OH:30])=[O:28])=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)=[O:10]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 8079CyclohexeneHCID 516892Sodium BicarbonateHCID 66640173HCID 66640173, compound

Product 1

HCID 66640067HCID 66640067, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

21 ml (0.22 Mol) borane dimethylsulfide complex are added dropwise during 15 min to an ice-cooled solution of 50.2 ml (495 mMol) cyclohexene in 400 ml of THF. The mixture is stirred for 2.5 h at rt and again cooled in an ice-bath. Then a solution of 23.29 g (82.5 mMol) trimethylsilanylethynyl-naphthalene-1-carboxylic acid methyl ester in 400 ml of THF is added dropwise. The mixture is warmed up to rt and stirred for 1 h. Then 585 ml sat. NaHCO3 solution and 138 ml H2O2 (30% in H2O) are added slowly (cool to keep temperature below 60° C.). The suspension is stirred for 16 h and then concentrated in vacuo. The residue is diluted with 1 l sat. NaHCO3 solution, 375 ml water and EtOAc, the organic layer is separated off and washed with 0.5 l sat. NaHCO3 solution and 250 ml water and discarded. The aq. phases are acidified by addition of 4 N HCl (pH=2) and extracted with 3 portions of EtOAc. The organic layers are dried (MgSO4) and concentrated. Trituration from hexane affords the title compound: MS: [M+1]+=245; HPLC: tRet=12.3.

Workup

  1. temperatureagain cooled in an ice-bath
  2. temperatureThe mixture is warmed up to rt
  3. stirringstirred for 1 h
  4. temperature(cool to keep temperature below 60° C.)
  5. stirringThe suspension is stirred for 16 h
  6. concentrationconcentrated in vacuo
  7. additionThe residue is diluted with 1 l sat. NaHCO3 solution, 375 ml water and EtOAc
  8. customthe organic layer is separated off
  9. washwashed with 0.5 l sat. NaHCO3 solution and 250 ml water
  10. additionThe aq. phases are acidified by addition of 4 N HCl (pH=2)
  11. extractionextracted with 3 portions of EtOAc
  12. dry with materialThe organic layers are dried (MgSO4)
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-3bd0c2ae84d7411e83a36002014b94ac
Source dataset
uspto-grants-2012_03
Patent number
US08133886B2

Reaction notes

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