Ethylene Oxide → Butyl ethyl(2-hydroxyethyl)phosphinate

HRID 1526925Notes

Reaction equation

HRID 1526925 reaction equation
[CH2:1]([P:3]([O-:9])[O:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:2].C([Li])CCC.B(F)(F)F.[CH3:19][CH2:20][O:21]CC.C1OC1.[Cl-].[NH4+]>C1(C)C=CC=CC=1.CCCCCC>[CH2:1]([P:3]([CH2:19][CH2:20][OH:21])(=[O:9])[O:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:2]

Participants

8

Reactant 5

HCID 6354Ethylene OxideHCID 8000Boron trifluoride etherateHCID 25517Ammonium ChlorideHCID 86614949Butyl ethyiphosphoniteHCID 178418339Butyllithium

Product 1

HCID 46832566Butyl ethyl(2-hydroxyethyl)phosphinateYield 73%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

4.5 g (30 mmol) of butyl ethylphosphonite (prepared as in Example 3) are dissolved in 30 ml of toluene and admixed at −78° C. with 12 ml (30 mmol) of a 2.5 molar solution of butyllithium in hexane. After 15 minutes 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 4.2 g (73% 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-46a121dfff0046719685cabdab5844be
Source dataset
uspto-grants-2015_07
Patent number
US09085734B2

Reaction notes

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