Diketene → n-Butyl ethyl(2-oxo-4-oxetanylmethyl)phosphinate

HRID 851452Notes

Reaction equation

HRID 851452 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[CH2:7]([P:9]([O-:15])[O:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH3:8]>>[CH2:7]([P:9]([CH2:1][CH:2]1[O:6][C:4](=[O:5])[CH2:3]1)(=[O:15])[O:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH3:8]

Participants

3

Reactant 2

HCID 12661DiketeneHCID 86614949Butyl ethyiphosphonite

Product 1

HCID 13718270n-Butyl ethyl(2-oxo-4-oxetanylmethyl)phosphinate

Conditions

Temperature
85 °C

Procedure

A solution of 0.98 parts of bis-(t-butylcyclohexyl)perdicarbonate in 12.6 parts of diketene was added dropwise over 1 hour to 90.2 parts of n-butyl ethylphosphonite which was vigorously stirred at 85° C. in a nitrogen atmosphere. After the addition the reaction mixture was passed down a wiped wall still at a temperature of 50° C. and a pressure of 0.13 mb to remove the excess phosphonite. The residue was distilled on the wiped wall still at a temperature of 75° C. and a pressure of 0.013 mb. The product n-butyl ethyl(2-oxo-4-oxetanylmethyl)phosphinate, was obtained as a colourless oil which the 31P NMR showed to be a nearly equal mixture of diastereoisomers having chemical shifts of δ-52.4 and δ-52.7 and which had the following elemental analysis by weight.

Workup

  1. additionAfter the addition the reaction mixture
  2. customstill at a temperature of 50° C.
  3. customa pressure of 0.13 mb to remove the excess phosphonite
  4. distillationThe residue was distilled on the wiped wall still at a temperature of 75° C.

Sources & evidence

ORD record
ord-3e61cf2b2f634d069668f4665510d16c
Source dataset
uspto-grants-1983_05
Patent number
US04384966

Reaction notes

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