Acetone → HCID 9899004, compound

HRID 729151Notes

Reaction equation

HRID 729151 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][P:5]([OH:7])[OH:6].[CH3:8][C:9]([CH3:11])=[O:10].C1OC1C>C[Si](C)(C)N[Si](C)(C)C.Cl.O.C(O)C>[NH2:1][CH2:2][CH2:3][CH2:4][P:5]([C:9]([OH:10])([CH3:11])[CH3:8])(=[O:7])[OH:6]

Participants

8

Reactant 3

HCID 180AcetoneHCID 6378Propylene OxideHCID 99892683-Amino-propanephosphonous

Product 1

HCID 9899004HCID 9899004, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent2×HCID 962WaterSolvent2×HCID 13838HexamethyldisilazaneSolvent

Procedure

A suspension of 1.23 g 3-aminopropylphosphonous acid in 25 ml of hexamethyldisilazane is heated to reflux under an inert gas for 20 hours. After this time a clear solution results and the reaction mixture is cooled to room temperature under inert gas and 50 ml of anhydrous acetone is added and an exothermic reaction results. The reaction mixture is allowed to cool to room temperature and the volatile components removed invacuo to afford a clear oil. This oil is dissolved in 50 ml of a 2.0M hydrochloric acid solution in water and washed with 2×100 ml of dichloromethane and 1×100 ml of ether. The aqueous layer is evaporated to dryness to give a semi-solid residue which is co-evaporated with water (10×20 ml) and absolute ethanol (10×20 ml) yielding3-aminopropyl(2-hydroxyprop-2-y)phosphinic acid hydrochloride m.p. 159°-161° as a white solid. This is suspended in absolute ethanol and treated with propylene oxide. Filtration and drying of the solid affords 3-aminopropyl(2-hydroxyprop-2 -yl)phosphinic acid; m.p. 243°-244°.

Workup

  1. temperatureis heated
  2. temperatureto reflux under an inert gas for 20 hours
  3. customAfter this time a clear solution results
  4. additionis added
  5. customan exothermic reaction
  6. customresults
  7. customthe volatile components removed invacuo
  8. customto afford a clear oil
  9. washwashed with 2×100 ml of dichloromethane and 1×100 ml of ether
  10. customThe aqueous layer is evaporated to dryness
  11. customto give a semi-solid residue which
  12. filtrationFiltration
  13. customdrying of the solid

Sources & evidence

ORD record
ord-38b6e166c57b4eaa8314d1ca29fc481a
Source dataset
uspto-grants-1991_09
Patent number
US05051524

Reaction notes

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