HCID 19993539, compound → HCID 19993529, compound

HRID 345055Notes

Reaction equation

HRID 345055 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][O:12][CH2:13][P:14](=[O:21])([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])C1C=CC=CC=1>[Pd].C(O)C.Cl>[OH:8][CH2:9][CH2:10][CH2:11][O:12][CH2:13][P:14](=[O:21])([O:15][CH2:16][CH3:17])[O:18][CH2:19][CH3:20]

Participants

5

Reactant 1

HCID 19993539HCID 19993539, compound

Product 1

HCID 19993529HCID 19993529, compoundYield 86.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

10% Palladium on charcoal (4.5 g) was added to a solution of diethyl 3-benzyloxypropoxymethylphosphonate (14.6 g, 46 mmol) in ethanol (250 ml) and 5M hydrochloric acid (4 ml) and the reaction stirred under an atmosphere of hydrogen for 6 h. The catalyst was removed by filtration through a glass-fibre paper and the ethanol evaporated under reduced pressure. The residue was then dissolved in chloroform, dried (MgSO4), filtered and reduced in vacuo to give diethyl 3-hydroxypropoxymethylphosphonate as a colourless oil (8.97 g, 86%); νmax (film) 3419, 2935, 1241, 1029 cm-1); δH (CDCl3) 1.46(6H, t, J7.1 Hz, (CH3CH2O)2), 83(2H, m, CH2CH2CH2), 3.73-3.79(5H, m, CH2CH2CH2 and OH (D2O exchangeable)), 3.81(2H, d, J7.9 Hz, CH2P), 4.18(4 H, m, (CH3CH2O)2).

Workup

  1. customThe catalyst was removed by filtration through a glass-fibre paper
  2. customthe ethanol evaporated under reduced pressure
  3. dissolutionThe residue was then dissolved in chloroform
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered

Sources & evidence

ORD record
ord-7f8ce67d498b47bea2ccc4210a7bdbfc
Source dataset
uspto-grants-1991_10
Patent number
US05055458

Reaction notes

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