1,2-Epoxybutane → HCID 9964348, compound

HRID 729148Notes

Reaction equation

HRID 729148 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][P:5]([OH:7])[OH:6].[O:8]1[CH:10]([CH2:11][CH3:12])[CH2:9]1>C[Si](C)(C)N[Si](C)(C)C.Cl.[I-].[Zn+2].[I-]>[NH2:1][CH2:2][CH2:3][CH2:4][P:5]([CH2:9][CH:10]([OH:8])[CH2:11][CH3:12])(=[O:7])[OH:6]

Participants

6

Reactant 2

HCID 78341,2-Epoxybutane2×HCID 99892683-Amino-propanephosphonous

Product 1

HCID 9964348HCID 9964348, compound

Reagents, catalysts & solvents 3

HCID 9883512zinc(II)iodideCatalystHCID 313Hydrochloric AcidSolventHCID 13838HexamethyldisilazaneSolvent

Procedure

A suspension of 2.46 g of 3-aminopropylphosphonous acid in 20 ml of hexamethyldisilazane is heated to reflux under an inert gas for 24 hours after which a clear solution results. The excess hexamethyldisilazane is removed by distillation at atmospheric pressure under a slight positive pressure of inert gas to afford a colourless oil. The oil is cooled to circa 40° and treated with 0.64 g of anhydrous zinc iodide and 25 ml of 1,2-epoxybutane. An exothermic reaction occurs and the epoxybutane refluxes. Reflux is continued for 6 hours after which time thin layer chromatography indicates the reaction to be complete. The reaction mixtureis filtered and the filtrate evaporated to dryness in vacuo at 40°. The residue is dissolved in water and stirred at room temperature for 1 hour and the water removed in vacuo to give an oily solid. This is dissolved in some 2.0M aqueous hydrochloric acid and washed with dichloromethane and ether. Removal of the water at 40° in vacuo affords a brown solid which is purified by ion-exchange chromatography on DOWEX® 50 W×8 (14-40 mesh) to give 3-aminopropyl(-2-hydroxybutyl)phosphinic acid, m.p. 184°-185°. as a white solid.

Workup

  1. temperatureis heated
  2. temperatureto reflux under an inert gas for 24 hours after which a clear solution
  3. customresults
  4. customThe excess hexamethyldisilazane is removed by distillation at atmospheric pressure under a slight positive pressure of inert gas
  5. customto afford a colourless oil
  6. temperatureThe oil is cooled to circa 40°
  7. customAn exothermic reaction
  8. temperatureReflux
  9. customthe reaction
  10. filtrationThe reaction mixtureis filtered
  11. customthe filtrate evaporated to dryness in vacuo at 40°
  12. dissolutionThe residue is dissolved in water
  13. customthe water removed in vacuo
  14. customto give an oily solid
  15. washwashed with dichloromethane and ether
  16. customRemoval of the water at 40° in vacuo
  17. customaffords a brown solid which
  18. customis purified by ion-exchange chromatography on DOWEX® 50 W×8 (14-40 mesh)

Sources & evidence

ORD record
ord-b931b56569e24aa4b590ee63ee1dcf50
Source dataset
uspto-grants-1991_09
Patent number
US05051524

Reaction notes

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