Sodium periodate → HCID 86658308, compound

HRID 885532Notes

Reaction equation

HRID 885532 reaction equation
[F:1][C:2]([F:20])([CH2:16][CH2:17][CH:18]=C)[CH2:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.I([O-])(=O)(=O)=[O:22].[Na+]>C1COCC1.O.[Os](=O)(=O)(=O)=O>[F:1][C:2]([F:20])([CH2:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:16][CH2:17][CH:18]=[O:22]

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 67246984HCID 67246984, compound

Product 1

HCID 86658308HCID 86658308, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Intermediate 16 (110 mg, 0.39 mmol) was dissolved in a mixture of THF (3 mL) and water (1 mL). To this solution was added sodium metaperiodate (272 mg, 1.27 mmol) and osmium tetroxide (4% water solution, 0.15 ml). The suspension was stirred 12 hours at room temperature, filtered and concentrated. The residue was purified by column chromatography on silica gel using methylene chloride/acetone (10:1) as eluent, to afford the title compound (89 mg, 81%) as oil.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2669cf9be2b14a9087588fbe2659d040
Source dataset
uspto-grants-2012_08
Patent number
US08242177B2

Reaction notes

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