Ethylene Oxide → Butyl ethyl(2-hydroxyethyl)phosphinate

HRID 878915Notes

Reaction equation

HRID 878915 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 (produced 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 stirring for 15 minutes 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 4.2 g (73% 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-68957e170a474ac28633c14723d63bbb
Source dataset
uspto-grants-2015_03
Patent number
US08987490B2

Reaction notes

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