HCID 22851231, compound → HCID 22851233, compound

HRID 1463784Notes

Reaction equation

HRID 1463784 reaction equation
C([O:8][CH2:9][C@@H:10]([O:12][CH2:13][P:14]([O:20][CH:21]([CH3:23])[CH3:22])([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])[CH3:11])C1C=CC=CC=1>[OH-].[OH-].[Pd+2].C(O)C.C1CCCCC=1>[CH:21]([O:20][P:14]([CH2:13][O:12][C@@H:10]([CH3:11])[CH2:9][OH:8])([O:16][CH:17]([CH3:18])[CH3:19])=[O:15])([CH3:22])[CH3:23]

Participants

4

Reactant 1

HCID 22851231HCID 22851231, compound

Product 1

HCID 22851233HCID 22851233, compoundYield 104.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 18676862Cyclohexene ethanolSolvent

Procedure

A solution of (S)-1-O-benzyl-2-O-[(diisopropylphosphono)methyl]-1,2-propanediol (8.20 g, 23.8 mmol) in 1:1 ethanol/cyclohexene (80 mL) was treated with 20% palladium hydroxide on carbon (4.0 g), and the mixture was heated at reflux for 18 hours. The reaction mixture was then filtered through a 1" pad of Celite, and the filtrate was concentrated in vacuo to give 6.3 g of the title compound as a clear, colorless oil which was used in the following reaction without purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 18 hours
  3. filtrationThe reaction mixture was then filtered through a 1" pad of Celite
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7f46e3e48c5c4caabe937a351adb4096
Source dataset
uspto-grants-1994_04
Patent number
US05302585

Reaction notes

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