Sodium Dithionite → HCID 19029819, compound

HRID 2256378Notes

Reaction equation

HRID 2256378 reaction equation
[CH3:1][C:2]1[CH:15]2[C:6]([CH3:21])([C:7]3[C:8](=[O:20])[CH:9]=[C:10]([CH:17]([CH3:19])[CH3:18])[C:11](=[O:16])[C:12]=3[CH2:13][CH2:14]2)[CH2:5][CH2:4][C:3]=1[C:22]([OH:24])=[O:23].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C1COCC1.O>[OH:20][C:8]1[CH:9]=[C:10]([CH:17]([CH3:19])[CH3:18])[C:11]([OH:16])=[C:12]2[C:7]=1[C:6]1([CH3:21])[CH:15]([CH2:14][CH2:13]2)[C:2]([CH3:1])=[C:3]([C:22]([OH:24])=[O:23])[CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 383736HCID 383736, compound

Product 1

HCID 19029819HCID 19029819, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 10 ml of THF was dissolved 300 mg of 3,4,4a,5,8,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-5,8-dioxo-2-phenanthrenecarboxylic acid obtained by the same extraction procedure as in Example 16, followed by addition of 16 ml of an aqueous solution containing 1.6 g of sodium dithionite, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with water and extracted with diethyl ether. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated. The resulting crude product was purified by silica gel column chromatography (eluent=chloroform:methanol=100:1) to provide 290 mg of 3,4,4a,9,10,10a-hexahydro-5,8-dihydroxy-1,4a-dimethyl-7-(1-methylethyl)-2-phenanthrenecarboxylic acid.

Workup

  1. customobtained by the same extraction procedure as in Example 16
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting crude product was purified by silica gel column chromatography (eluent=chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-34279e6077554afc81f38c42ffc372df
Source dataset
uspto-grants-1997_08
Patent number
US05654343

Reaction notes

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