Water → 1,1-Diethoxyethyl(cyclohexylmethyl)phosphinic acid ethyl ester

HRID 1729186Notes

Reaction equation

HRID 1729186 reaction equation
[H-].[Na+].[CH2:3]([O:5][PH:6]([C:8]([O:13][CH2:14][CH3:15])([O:10][CH2:11][CH3:12])[CH3:9])=[O:7])[CH3:4].Br[CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.O>O1CCCC1>[CH2:3]([O:5][P:6]([C:8]([O:13][CH2:14][CH3:15])([O:10][CH2:11][CH3:12])[CH3:9])([CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:7])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 137636Cyclohexane, (bromomethyl)-HCID 178476820HCID 178476820, compound

Product 1

HCID 117226951,1-Diethoxyethyl(cyclohexylmethyl)phosphinic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

21 g of 99% sodium hydride are suspended at room temperature under argon in 1000 ml of anhydrous tetrahydrofuran, and a solution of 172.2 g of 1,1-diethoxyethylphosphinic acid ethyl ester is added dropwise over a period of 2.5 hours, the temperature being maintained at from 20° to 25°. The reaction is exothermic and involves the evolution of gas. The batch is then stirred for 1.5 hours at room temperature, 142.2 g of bromomethylcyclohexane are added and heating under reflux is effected for 24 hours. The suspension is cooled to 4° and 250 ml of water are carefully added. Two phases are formed. The tetrahydrofuran phase is separated off and the aqueous phase is extracted twice with 250 ml of dichloromethane each time. Concentration by evaporation yields a brown oil which, after distillation under reduced pressure, gives 1,1-diethoxyethyl(cyclohexylmethyl)phosphinic acid ethyl ester having a boiling point of 95° (1.8×10-4 mbar).

Workup

  1. temperaturethe temperature being maintained at from 20° to 25°
  2. temperatureheating
  3. temperatureunder reflux
  4. waitis effected for 24 hours
  5. temperatureThe suspension is cooled to 4°
  6. customTwo phases are formed
  7. customThe tetrahydrofuran phase is separated off
  8. extractionthe aqueous phase is extracted twice with 250 ml of dichloromethane each time
  9. concentrationConcentration
  10. customby evaporation
  11. customyields a brown oil which
  12. distillationafter distillation under reduced pressure

Sources & evidence

ORD record
ord-99158b2de74644b38953a6f97e5a1980
Source dataset
uspto-grants-1994_07
Patent number
US05332729

Reaction notes

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