Chloroform → HCID 9813169, compound

HRID 2050702Notes

Reaction equation

HRID 2050702 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][P:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:10])[O:6]C(C)C.C(Cl)(Cl)Cl.C[Si](Br)(C)C>C(O)(C)C.C1OC1C>[NH2:1][CH2:2][CH2:3][CH2:4][P:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:6])[OH:10]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 76113BromotrimethylsilaneHCID 19090927HCID 19090927, compound

Product 1

HCID 9813169HCID 9813169, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6378Propylene OxideSolvent

Procedure

To a solution of 5.7 g (0.0224 mol) of isopropyl 3-aminopropyl(benzyl)phosphinate in 50 ml of chloroform 9.91 ml (0.0922 mol) of trimethylsilylbromide are added raising the temperature to 44°. The reaction mixture is stirred at 50° for 4 hours and then at room temperature overnight. Removal of the chloroform and excess trimethylsilylbromide under reduced pressure yields an oil which is taken up in isopropanol and 20 ml of propylene oxide. After stirring for 10 minutes, a white solid precipitates. The solid is filtered off and dried over phosphorous pentoxide yielding 3-aminopropyl(benzyl)phosphinic acid, m.p. 278-280°.

Workup

  1. temperatureraising the temperature to 44°
  2. customat room temperature
  3. customovernight
  4. customRemoval of the chloroform and excess trimethylsilylbromide under reduced pressure
  5. customyields an oil which
  6. stirringAfter stirring for 10 minutes
  7. customa white solid precipitates
  8. filtrationThe solid is filtered off
  9. dry with materialdried over phosphorous pentoxide

Sources & evidence

ORD record
ord-8bfb170ac6bc46a997e5026c3aa92ebc
Source dataset
uspto-grants-1991_05
Patent number
US05013863

Reaction notes

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