Réaction #56606

ord-f22f27baf214491bb600c143b331795b

Équation de réaction

COC(=O)CCc1cc(-n2nc3ccc(S(=O)(=O)c4ccccc4)cc3n2)c(O)c(C(C)(C)C)c1
Methyl 3-(5-phenylsulfonylbenzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydro-cinnamate
CN1C(C)(C)CC(O)CC1(C)C
1,2,2,6,6-pentamethyl-4-hydroxy-piperidine
CCCCCCC[CH2][Sn](=[O])[CH2]CCCCCCC
dioctyltin oxide
CN1C(C)(C)CC(OC(=O)CCc2cc(-n3nc4ccc(S(=O)(=O)c5ccccc5)cc4n3)c(O)c(C(C)(C)C)c2)CC1(C)C
title compound
Rendement 70.0%
CN1C(C)(C)CC(OC(=O)CCc2cc(-n3nc4ccc(S(=O)(=O)c5ccccc5)cc4n3)c(O)c(C(C)(C)C)c2)CC1(C)C
1,2,2,6,6-Pentamethylpiperidin-4-yl 3-(5-Phenylsulfonylbenzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate
Rendement 70.0%

Conditions de réaction

Température
160°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreAt the end of six hours, any remaining xylene is removed by distillation under vacuum
  2. 2
    AutreThe crude yellow oil obtained
  3. 3
    Autreis chromatographed through a pad of silica gel

Mode opératoire

Methyl 3-(5-phenylsulfonylbenzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydro-cinnamate (5 g, 0.01 mol), xylenes (18 g, 0.17 mol), 1,2,2,6,6-pentamethyl-4-hydroxy-piperidine (2.1 g, 0.012 mol) and dioctyltin oxide (0.5 g, 0.0014 mol) are charged to a reactor and heated to 160° C. while being vigorously stirred. At the end of six hours, any remaining xylene is removed by distillation under vacuum. The crude yellow oil obtained is chromatographed through a pad of silica gel using ethyl aetate as the eluent. The title compound is obtained in a 70% yield as a low melting yellow solid, melting at 45-52° C., whose structure is consistent with 1Hnmr and mass spectrometry.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07419513B2uspto-grants-2008_09