Ethylene Oxide → Butyl ethyl(2-hydroxyethyl)phosphinate

HRID 878916Notes

Reaction equation

HRID 878916 reaction equation
[CH2:1]([P:3]([O-:9])[O:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:2].[H-].[Na+].B(F)(F)F.[CH3:16][CH2:17][O:18]CC.C1OC1.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[CH2:1]([P:3]([CH2:16][CH2:17][OH:18])(=[O:9])[O:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:2]

Participants

7

Reactant 5

HCID 6354Ethylene OxideHCID 8000Boron trifluoride etherateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86614949Butyl ethyiphosphonite

Product 1

HCID 46832566Butyl ethyl(2-hydroxyethyl)phosphinateYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.5 g (30 mmol) of butyl ethylphosphonite (produced as in Example 2) are dissolved in 30 ml of toluene and at 0° C. admixed with 0.72 g (30 mmol) of sodium hydride. After stirring for one hour 5.68 g (40 mmol) of boron trifluoride etherate are added and ethylene oxide is passed in followed by further reaction for two hours. Then, aqueous ammonium chloride solution is added followed by warming to room temperature. This is followed by concentrating in vacuo, taking up in diethyl ether, removal of insoluble salts by filtration and renewed concentrating. Chromatographic purification leaves 4.5 g (78% of theory) of butyl ethyl(2-hydroxyethyl)phosphinate as oil.

Workup

  1. additionare added
  2. customin followed by further reaction for two hours
  3. concentrationby concentrating in vacuo
  4. customremoval of insoluble salts
  5. filtrationby filtration
  6. concentrationrenewed concentrating
  7. customChromatographic purification

Sources & evidence

ORD record
ord-4ecf0f5430f84ca78367a5786f27afc4
Source dataset
uspto-grants-2015_03
Patent number
US08987490B2

Reaction notes

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