HCID 14497596, compound → HCID 14497602, compound
Reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:23]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[N:22]=[C:21]([CH2:32][CH2:33][CH:34]([OH:36])[CH3:35])[CH:20]=2)=[CH:15][CH:14]=1>C(Cl)Cl>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[N:23]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[N:22]=[C:21]([CH2:32][CH2:33][C:34](=[O:36])[CH3:35])[CH:20]=2)=[CH:17][CH:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of pyridinium chlorochromate (3.65 g, 16.93 mM) in CH2Cl2 (20 ml) was added the alcohol 20, (3.02 g, 8.46 mM) in CH2Cl2 (15 ml). After stirring for 4 hours, the reaction solution was decanted from the chromium precipitates that were washed with EtOAc (2×150 ml). The reaction solution and the washes were combined, filtered through florosil, and concentrated in vacuo. Chromatography (120 g, Baker 40 gm silica gel) with Et2O:hexane (1:1 to 100% Et2O) as eluent, followed by crystallization from Et2O:hexane afforded 23, (2.09 g, 70%) as a white crystalline solid, mp=85°-86° C.