Diketene → Isobutyl methyl(2-oxo-4-oxetanylmethyl)phosphinate

HRID 851455Notes

Reaction equation

HRID 851455 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[CH3:7][P:8]([O-:14])[O:9][CH2:10][CH:11]([CH3:13])[CH3:12]>>[CH3:7][P:8]([CH2:1][CH:2]1[O:6][C:4](=[O:5])[CH2:3]1)(=[O:14])[O:9][CH2:10][CH:11]([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 12661DiketeneHCID 86741778Isobutyl methanephosphonite

Product 1

HCID 13718269Isobutyl methyl(2-oxo-4-oxetanylmethyl)phosphinate

Procedure

A mixture of 4.2 parts of diketene and 0.33 parts of bis-(t-butylcyclohexyl)perdicarbonate was added dropwise over 1 hour to 27.2 parts of vigorously stirred isobutyl methylphosphonite which was heated at 85° 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° and a pressure of 0.13 mb. The product isobutyl methyl(2-oxo-4-oxetanylmethyl)phosphinate was obtained as a colourless oil with a characteristic infra-red band at 1820 cm-1.

Workup

  1. temperaturewas heated at 85° in a nitrogen atmosphere
  2. additionAfter the addition the reaction mixture
  3. customa wiped-wall still at a temperature of 50° C.
  4. customa pressure of 0.13 mb to remove the excess phosphonite
  5. distillationThe residue was distilled on the wiped wall still at a temperature of 75°

Sources & evidence

ORD record
ord-587b7b20a02f4c6aae0fd05360cc0b29
Source dataset
uspto-grants-1983_05
Patent number
US04384966

Reaction notes

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