Hydrogen Peroxide → HCID 86750803, compound

HRID 1941184Notes

Reaction equation

HRID 1941184 reaction equation
[CH3:1][C@@H:2]1[C@:24]2([O:30][CH2:29][C@H:27]([CH3:28])[CH2:26][CH2:25]2)[O:23][C@H:4]2[CH2:5][C@@H:6]3[C@@:20]([CH3:21])([C@@H:3]12)[CH2:19][CH2:18][C@H:17]1[C@H:7]3[CH2:8][CH2:9][C@@H:10]2[C@:15]1([CH3:16])[CH:14]=[CH:13][C:12](=[O:22])[CH2:11]2.[O:31]1CCCC1.[OH-].[Na+].OO>C(OCC)(=O)C.CO>[O:31]1[C@H:13]2[C:12](=[O:22])[CH2:11][C@H:10]3[C@:15]([CH3:16])([C@@H:14]12)[C@@H:17]1[C@H:7]([C@H:6]2[C@:20]([CH3:21])([CH2:19][CH2:18]1)[C@H:3]1[C@@H:2]([C@:24]4([O:30][CH2:29][C@H:27]([CH3:28])[CH2:26][CH2:25]4)[O:23][C@H:4]1[CH2:5]2)[CH3:1])[CH2:8][CH2:9]3

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 5384732154462-55-4

Product 1

HCID 86750803HCID 86750803, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (5α,25R)-spirost-1-en-3-one (2.87 g, 6.96 mmol), tetrahydrofuran (30 mL), methanol (50 mL) and 15% sodium hydroxide (1 mL) was stirred under nitrogen atmosphere. The mixture was cooled to 0° C. and 30% hydrogen peroxide (5 mL) was added. The reaction mixture was gradually warmed to room temperature and stirred for 4 hours. The reaction was diluted with ethyl acetate, cooled to 0° C., and then quenched with saturated sodium bisulfite solution. The mixture was washed with saturated sodium bisulfite (2×), brine (1×), dried (sodium sulfate), filtered and concentrated in vacuo to give 2.64 g, (88%) of the title compound.

Workup

  1. temperatureThe reaction mixture was gradually warmed to room temperature
  2. stirringstirred for 4 hours
  3. temperaturecooled to 0° C.
  4. customquenched with saturated sodium bisulfite solution
  5. washThe mixture was washed with saturated sodium bisulfite (2×), brine (1×)
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cbc90c842c7244a5ba205c2b220bb4b1
Source dataset
uspto-grants-1997_12
Patent number
US05703052

Reaction notes

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