تفاعل #485953

ord-f3a35720baf943ee80a3392cf1ad26e8

معادلة التفاعل

CCOP(=O)(CO)OCC
hydroxymethyl phosphonic acid diethylester
ClC/C=C\CCl
Z-1,4-dichloro-2-butene
[H-].[Na+]
sodium hydride
[Cl-].[NH4+]
ammonium chloride
CCOP(=O)(COC/C=C\CCl)OCC
title product
CCOP(=O)(COC/C=C\CCl)OCC
Z-(4-Chloro-2-butenyloxy)methyl phosphonic acid diethylester

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.ADDITIONis added at 0° C
  2. 2
    استخلاصextracted with diethylether

الإجراء التجريبي

To a mixture of hydroxymethyl phosphonic acid diethylester (1.68 g, 10 mmol), Z-1,4-dichloro-2-butene (1.9 g, 15 mmol) and tetra-n-butylammonium iodide (0.36 g, 1 mmol) in anhydrous tetrahydrofuran (15 ml), sodium hydride (0.48 g, 12 mmol, 60% in oil) is added at 0° C. The resulting mixture is stirred overnight at 20° C., hydrolyzed with a saturated solution of ammonium chloride and extracted with diethylether. The title product is obtained by flash chromatography on silica gel (1.2 g, 45%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05817647uspto-grants-1998_10