Acetone → HCID 86744760, compound

HRID 2050721Notes

Reaction equation

HRID 2050721 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][P:5]([OH:7])[OH:6].[CH3:8][C:9]([CH3:11])=[O:10].C(O)C.[ClH:15]>C[Si](C)(C)N[Si](C)(C)C.O>[ClH:15].[NH2:1][CH2:2][CH2:3][CH2:4][P:5]([C:9]([OH:10])([CH3:11])[CH3:8])(=[O:7])[OH:6]

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 702EthanolHCID 99892683-Amino-propanephosphonous

Product 1

HCID 86744760HCID 86744760, compound

Reagents, catalysts & solvents 2

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 in vacuo to afford a clear oil. This oil is dissolved in 50 ml of a 2.0 M 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) yielding 3-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 in vacuo
  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

Sources & evidence

ORD record
ord-352ac8b00deb4eb8b1ff8eca5a271b16
Source dataset
uspto-grants-1991_05
Patent number
US05013863

Reaction notes

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