Iodine → HCID 54512316, compound

HRID 975163Notes

Reaction equation

HRID 975163 reaction equation
[BH4-].[Na+].II.[C:5]([C:8]1[CH:9]=[CH:10][C:11]2[C:17](=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:16]3[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=3[CH2:14][O:13][C:12]=2[CH:28]=1)(O)=[O:6]>C1COCC1.C(OCC)(=O)C>[OH:6][CH2:5][C:8]1[CH:9]=[CH:10][C:11]2[C:17](=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:16]3[CH:24]=[CH:25][CH:26]=[CH:27][C:15]=3[CH2:14][O:13][C:12]=2[CH:28]=1

Participants

6

Reactant 3

HCID 807IodineHCID 4311764Sodium borohydrideHCID 53813644HCID 53813644, compound

Product 1

HCID 54512316HCID 54512316, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (2.22 g) was dissolved in 300 ml of THF, and 7.45 g of iodine was added to the solution under ice cooling. Then, 300 ml of a solution of 7.63 g of Compound 1-a in THF was added under the same conditions and the mixture was stirred at room temperature overnight, followed by addition of ice chips. The mixture was then diluted with ethyl acetate, and the organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [eluent: chloroform] to give 6.58 g (90.2%) of the product as a colorless oily substance.

Workup

  1. additionfollowed by addition of ice chips
  2. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography [eluent: chloroform]

Sources & evidence

ORD record
ord-f06ee5f629d8445b90153c6f285eb2e9
Source dataset
uspto-grants-1997_03
Patent number
US05607955

Reaction notes

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