Diethyl {[di(prop-2-en-1-yl)amino]methyl}phosphonate → Diethyl [(1H-pyrrol-1-yl)methyl]phosphonate

HRID 2247148Notes

Reaction equation

[CH2:1]([N:4]([CH2:8][P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])[CH2:5][CH:6]=[CH2:7])C=C>ClC1C=CC=CC=1>[N:4]1([CH2:8][P:9](=[O:16])([O:10][CH2:11][CH3:12])[O:13][CH2:14][CH3:15])[CH:1]=[CH:7][CH:6]=[CH:5]1

Participants

Conditions

Temperature: 60 °C

Procedure

0.1 g (0.41 mmole) of the diethyl diallylaminomethylphosphonate prepared in example 25 was dissolved in 2 ml chlorobenzene, then 0.014 g (0.02 mmole) of the bimetallic ruthenium complex 3.e prepared in example 24 was added and the mixture was stirred for 16 hours at 60° C. The catalyst was removed after evaporation of the chlorobenzene by column chromatography, yielding 0.04 g (0.18 mmole, yield 45%) diethyl 1H-pyrrole-1-ylmethylphosphonate. This product was further characterised by the following spectra:

Workup

customThe catalyst was removed
customafter evaporation of the chlorobenzene by column chromatography

Sources & evidence

ORD record: ord-2aa35d15fdfb4201b8aba3084e1d5d09
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687635B2

Reaction notes

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