3-Oxazolidineethanol → Diethyl P-((bis(2-hydroxyethyl)amino)methyl)phosphonate

HRID 61320Notes

Reaction equation

HRID 61320 reaction equation
[P:1]([O-:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].[O:9]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][OH:16])[CH2:10]1>>[OH:9][CH2:13][CH2:12][N:11]([CH2:10][P:1](=[O:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4])[CH2:14][CH2:15][OH:16]

Participants

3

Reactant 2

HCID 600463-OxazolidineethanolHCID 3780918Diethylphosphite

Product 1

HCID 17722Diethyl P-((bis(2-hydroxyethyl)amino)methyl)phosphonate

Conditions

Temperature
60 °C

Procedure

Diethyl phosphite (2.5 mol, 352/3 g) was added slowly to a mixture of the product from stage (1.1) and Amberlight™ IR120 resin—acid form (available from Aldrich, 100 g) to form a reaction mixture. On completion of the addition, the reaction mixture was stirred at 60° C. for 2 hours and then allowed to cool to a temperature of 25° C. The product was extracted with a 2:1 mixture of diethyl ether and ethyl acetate (5×300 ml), the combined extracts were dried over magnesium sulphate and evaporated to give 354 g of diethyl [bis(2-hydroxyethyl)amino]methylphosphonate in the form of a pale yellow liquid. The product was stored over 4A molecular sieves. This was designated Monomer (1).

Workup

  1. customto form a reaction mixture
  2. additionOn completion of the addition
  3. temperatureto cool to a temperature of 25° C
  4. extractionThe product was extracted with a 2:1 mixture of diethyl ether and ethyl acetate (5×300 ml)
  5. dry with materialthe combined extracts were dried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-9225e434967d4febbd80c4bc1d3dc29b
Source dataset
uspto-grants-2016_09
Patent number
US09441121B2

Reaction notes

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