Hydrogen Peroxide → HCID 15703880, compound

HRID 1534377Notes

Reaction equation

HRID 1534377 reaction equation
[CH2:1]([O:3][C:4]1[C:15]2[O:14][C:13]3[CH:16]=[CH:17][C:18]([C:22](=[CH2:27])[CH2:23][CH:24]([CH3:26])[CH3:25])=[C:19]([O:20][CH3:21])[C:12]=3[C:11](=[O:28])[O:10][CH2:9][C:8]=2[CH:7]=[C:6]([CH3:29])[CH:5]=1)[CH3:2].[OH-:30].[Na+].OO>CCCCCC.O1CCCC1.C(O)C>[CH2:1]([O:3][C:4]1[C:15]2[O:14][C:13]3[CH:16]=[CH:17][C:18]([CH:22]([CH2:27][OH:30])[CH2:23][CH:24]([CH3:25])[CH3:26])=[C:19]([O:20][CH3:21])[C:12]=3[C:11](=[O:28])[O:10][CH2:9][C:8]=2[CH:7]=[C:6]([CH3:29])[CH:5]=1)[CH3:2]

Participants

7

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 15703884HCID 15703884, compound

Product 1

HCID 15703880HCID 15703880, compound

Reagents, catalysts & solvents 3

HCID 702EthanolCatalystHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

2 ml (1 mmol) of a 0.5 M 9-borabicyclo-3.3.1-nonane solution in hexane are added dropwise under argon to a solution of 130 mg (0.33 mmol) of the compound from Example 148 in 4 ml of absolute tetrahydrofuran. After 14 h at room temperature, a few drops of ethanol, 2 ml of 2 N sodium hydroxide solution and 0.5 ml of 30% strength hydrogen peroxide solution are added. The mixture is stirred vigorously for 3 h and then concentrated carefully and the residue is taken up in dichloromethane. The solution is washed with water, and the organic phase is dried over magnesium sulphate and concentrated, and the residue is purified by column chromatography on silica gel using petroleum ether/ethyl acetate 6:1.

Workup

  1. concentrationconcentrated carefully
  2. washThe solution is washed with water
  3. dry with materialthe organic phase is dried over magnesium sulphate
  4. concentrationconcentrated
  5. customthe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-89b8fc7a7740433a9f96ff4a97bbeaa2
Source dataset
uspto-grants-1992_02
Patent number
US05089487

Reaction notes

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