Potassium Iodide → HCID 9937956, compound

HRID 478941Notes

Reaction equation

HRID 478941 reaction equation
C(O[C@@H:8]1[O:34][C@H:33]([C:35]([O:37][CH3:38])=[O:36])[C@@H:25]([O:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[C@H:17]([O:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[C@H:9]1[O:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])(=O)C(C)(C)C.[I-:39].[K+].B(F)(F)F.CCOCC.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(#N)C>[I:39][C@H:8]1[O:34][C@H:33]([C:35]([O:37][CH3:38])=[O:36])[C@@H:25]([O:26][C:27](=[O:32])[C:28]([CH3:30])([CH3:29])[CH3:31])[C@H:17]([O:18][C:19](=[O:24])[C:20]([CH3:21])([CH3:22])[CH3:23])[C@H:9]1[O:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:13])[CH3:14]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 8000Boron trifluoride etherateHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 11341774HCID 11341774, compound

Product 1

HCID 9937956HCID 9937956, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 1,2,3,4-tetra-O-pivaloyl-β-D-glucopyranuronate (2.72 g, 5 mmol) in acetonitrile (10 cm3) was heated and stirred at gentle reflux under argon with potassium iodide (1.66 g, 10 mmol) and boron trifluoride diethyl etherate (2.50cm3). After 1 h the dark mixture was cooled, then 10% aq. sodium thiosulfate (25 cm3) and saturated aqueous sodium bicarbonate (NaHCO3) (25 cm3) were added and the product was extracted using ethyl acetate (50 cm3+20 cm3). The combined organic phases were washed with further NaHCO3, water and brine, then dried over anhydrous Na2SO4 and evaporated to an orange gum (2.8 g). Triuration with ethanol gave a crystalline product; evaporation of the mother liquors, followed by chromatography on silica gel, eluting with 10% ethyl acetate in hexane, afforded further product of equal purity; combined yield, 1.89 g (66%), m.p. 98-100° C.; δH (220 MHz, CDC13) 1.10-1.30 (27H, 3s), 3.73 (3H, s), 4.26 (1H, dd), 4.35 (1H, d), 5.22, 5.61 (2H, 2t) and 7.04 (1H, d).

Workup

  1. temperatureAfter 1 h the dark mixture was cooled
  2. extractionthe product was extracted
  3. washThe combined organic phases were washed with further NaHCO3, water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated to an orange gum (2.8 g)
  6. customTriuration with ethanol gave a crystalline product
  7. customevaporation of the mother liquors
  8. washeluting with 10% ethyl acetate in hexane
  9. customafforded further product of equal purity
  10. customcombined yield

Sources & evidence

ORD record
ord-8699dbe7a9174064bed4ffbbedda263f
Source dataset
uspto-grants-2003_11
Patent number
US06642366B1

Reaction notes

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