Water → HCID 20034698, compound

HRID 231199Notes

Reaction equation

HRID 231199 reaction equation
C([CH:4]([C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=1)[C:5]([CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=1)=[O:6])C=C.[O:32]1CC[CH2:34][CH2:33]1.O.I([O-])(=O)(=O)=O.[Na+]>C(O)(C)(C)C.[Os](=O)(=O)(=O)=O>[CH3:27][O:26][C:24]1[CH:25]=[C:20]([CH:4]([C:5](=[O:6])[CH2:7][C:8]2[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=2)[CH2:34][CH2:33][OH:32])[CH:21]=[C:22]([O:30][CH3:31])[C:23]=1[O:28][CH3:29]

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 20034695HCID 20034695, compoundHCID 23667635Sodium periodate

Product 1

HCID 20034698HCID 20034698, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolvent

Procedure

To a solution of 27.5 g of the compound prepared in (d) above in 640 ml of a mixture of tetrahydrofuran and water (in a 2:1 ratio) was added 9 ml of a 2.5% solution of osmium tetraoxide in tert.-butanol. The reaction mixture was then allowed to stir at room temperature until it darkened to a black opaque mixture, after which time 82.07 g of sodium metaperiodate was added. The resultant mixture was then stirred at room temperature for 20 hours, after which time it was filtered and the solvent was removed by evaporation to yield a residue that was extracted with a mixture of ethyl acetate and water. The organic layer was evaporated and the resultant residue was chromatographed on silica gel employing a mixture of methylene chloride and ethyl acetate in a ratio of 8:1 as the eluent to yield a solid.

Workup

  1. filtrationafter which time it was filtered
  2. customthe solvent was removed by evaporation
  3. customto yield a residue that
  4. extractionwas extracted with a mixture of ethyl acetate and water
  5. customThe organic layer was evaporated
  6. customthe resultant residue was chromatographed on silica gel employing
  7. additiona mixture of methylene chloride and ethyl acetate in a ratio of 8:1 as the eluent
  8. customto yield a solid

Sources & evidence

ORD record
ord-b18dac198ccf4b2eaa717f3fa807e3b8
Source dataset
uspto-grants-1989_07
Patent number
US04845129

Reaction notes

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