Ethylene Oxide → Butyl ethyl(2-hydroxyethyl)phosphinate

HRID 1526926Notes

Reaction equation

HRID 1526926 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 (prepared 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 one hour of stirring, 5.68 g (40 mmol) of boron trifluoride etherate are added and ethylene oxide is passed in and the mixture is subsequently reacted for a further two hours. Thereafter, aqueous ammonium chloride solution is added and the mixture is warmed to room temperature. That is subsequently concentrated in vacuo, the residue is taken up in diethyl ether, insoluble salts are filtered off and the mixture is again concentrated. Chromatographic purification leaves 4.5 g (78% of theory) of butyl ethyl(2-hydroxyethyl)phosphinate being obtained as oil.

Workup

  1. customis subsequently reacted for a further two hours
  2. concentrationThat is subsequently concentrated in vacuo
  3. filtrationinsoluble salts are filtered off
  4. concentrationthe mixture is again concentrated
  5. customChromatographic purification

Sources & evidence

ORD record
ord-1113067926c64182b9c948538c2cb9cb
Source dataset
uspto-grants-2015_07
Patent number
US09085734B2

Reaction notes

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