Water → Ethyl diethoxymethyl(cyclohexylmethyl)phosphinate

HRID 1492968Notes

Reaction equation

HRID 1492968 reaction equation
[CH2:1]([O:3][PH:4]([CH:6]([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9])=[O:5])[CH3:2].[H-].[Na+].Br[CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.O>O1CCCC1>[CH2:1]([O:3][P:4]([CH:6]([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9])([CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 137636Cyclohexane, (bromomethyl)-HCID 178472284HCID 178472284, compound

Product 1

HCID 19090914Ethyl diethoxymethyl(cyclohexylmethyl)phosphinate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon, a solution of 221 g of diethoxymethylphosphinic acid ethyl ester in 1000 ml of tetrahydrofuran is added dropwise in the course of 3 hours to a suspension of 26.4 g of 99% sodium hydride in 1500 ml of tetrahydrofuran, the temperature being maintained at 20°-25°. The reaction is exothermic and is associated with the evolution of gas. The mixture is stirred for 2 hours at room temperature and the 177.1 g of bromomethylcyclohexane are added in the course of 20 minutes; the mixture is stirred at reflux for 24 hours, then cooled to 0°, and 200 ml of water are carefully added. The solvent is removed under reduced pressure and the residue is partitioned between dichloromethane and water. The organic phase is separated off, dried over sodium sulfate and concentrated by evaporation under reduced pressure. The oil that remains behind is distilled under reduced pressure and yields diethoxymethyl(cyclohexylmethyl)phosphinic acid ethyl ester having a boiling point of 85° (6×10-4 bar).

Workup

  1. temperaturethe temperature being maintained at 20°-25°
  2. stirringthe mixture is stirred
  3. temperatureat reflux for 24 hours
  4. temperaturecooled to 0°
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is partitioned between dichloromethane and water
  7. customThe organic phase is separated off
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated by evaporation under reduced pressure
  10. distillationThe oil that remains behind is distilled under reduced pressure

Sources & evidence

ORD record
ord-de366009b4ab440ebcaa5fb21dd9fd6b
Source dataset
uspto-grants-1994_12
Patent number
US05376684

Reaction notes

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