Lithium hydroxide, monohydrate → HCID 9877609, compound

HRID 1463611Notes

Reaction equation

HRID 1463611 reaction equation
O.[OH-].[Li+].C([O:6][P:7]([CH2:14][CH2:15][CH2:16][NH2:17])([CH:9]1[CH2:13][CH2:12][CH2:11][O:10]1)=[O:8])C>O.C(O)C>[NH2:17][CH2:16][CH2:15][CH2:14][P:7]([CH:9]1[CH2:13][CH2:12][CH2:11][O:10]1)(=[O:6])[OH:8]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10059358HCID 10059358, compound

Product 1

HCID 9877609HCID 9877609, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of 0.57 g of lithium hydroxide monohydrate in 10 ml of water is added a solution of 2.0 g of ethyl-3-aminopropyl(tetrahydrofuran-2-yl)phosphinate in 20 ml of ethanol. A slight exothermic reaction ensues and the reaction mixture becomes turbid. A further 5 ml of water is added and the then clear solution stirred for 3 days at room temperature. After this time, the reaction mixture is concentrated in vacuo at 55°. The residue is re-dissolved in water and washed with 3×10 ml of dichloromethane. The aqueous layer is again evaporated to dryness and the residue dissolved in 10 ml of water and treated with 0.65 ml of 85% phosphoric acid in 2 ml of water. After stirring overnight, the solid is removed by filtration. Evaporation of the filtrate and crystallisation of the residue from methanol/ether affords 3-aminopropyl(tetrahydrofuran-2-yl)phosphinic acid, m.p. 222°-223° (dec.), as a white solid.

Workup

  1. customA slight exothermic reaction ensues
  2. concentrationAfter this time, the reaction mixture is concentrated in vacuo at 55°
  3. dissolutionThe residue is re-dissolved in water
  4. washwashed with 3×10 ml of dichloromethane
  5. customThe aqueous layer is again evaporated to dryness
  6. dissolutionthe residue dissolved in 10 ml of water
  7. additiontreated with 0.65 ml of 85% phosphoric acid in 2 ml of water
  8. stirringAfter stirring overnight
  9. customthe solid is removed by filtration
  10. customEvaporation of the filtrate and crystallisation of the residue from methanol/ether

Sources & evidence

ORD record
ord-5597f61dd7b64b3996c9ddb764c9b707
Source dataset
uspto-grants-1994_04
Patent number
US05300679

Reaction notes

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