HCID 21468036, compound → HCID 22880064, compound

HRID 1939707Notes

Reaction equation

HRID 1939707 reaction equation
C([O:8][CH2:9][CH2:10][CH:11]([O:17][CH2:18][P:19]([O:25][CH:26]([CH3:28])[CH3:27])([O:21][CH:22]([CH3:24])[CH3:23])=[O:20])[CH2:12][O:13][CH2:14][O:15][CH3:16])C1C=CC=CC=1>C(O)C.C1CCCCC=1.[OH-].[OH-].[Pd+2]>[CH:22]([O:21][P:19]([CH2:18][O:17][C@@H:11]([CH2:10][CH2:9][OH:8])[CH2:12][O:13][CH2:14][O:15][CH3:16])([O:25][CH:26]([CH3:28])[CH3:27])=[O:20])([CH3:24])[CH3:23]

Participants

5

Reactant 1

HCID 21468036HCID 21468036, compound

Product 1

HCID 22880064HCID 22880064, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 8079CyclohexeneSolvent

Procedure

Palladium hydroxide on carbon (20%, 10 g) was added to a solution of 4-O-benzyl-2-O-(diisopropylphosphonomethyl)-1-O-methoxymethyl-1,2,4-butanetriol (21.9 g, 52.33 mmol) in a mixture of ethanol and cyclohexene (200 mL of each). The resulting mixture was heated at reflux for 6 hours. The mixture was cooled to room temperature and filtered. The filtrate was evaporated and the residue was purified by flash chromatography on silica gel (methylene chloride:methanol=20:1 to 10:1) to give 16.79 g (98% yield) of the title compound as an oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 6 hours
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customthe residue was purified by flash chromatography on silica gel (methylene chloride:methanol=20:1 to 10:1)

Sources & evidence

ORD record
ord-09a3e13f2c964fa182aba327dc807f01
Source dataset
uspto-grants-1997_12
Patent number
US05696263

Reaction notes

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