Cornforth reagent → HCID 57517436, compound
Reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH2:19][OH:20])=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([CH:19]=[O:20])=[CH:16][CH:17]=3)[CH2:12][CH2:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
molecular sieves (0.63 g) were added to a solution of 12 (0.24 g, 0.83 mmol) in CH2Cl2 (10 mL), PDC (0.63 g, 1.66 mmol). The mixture was stirred at room temperature overnight before it was filtered through celite. The organic layer was concentrated under reduced pressure then purified by silica gel chromatography (EtOAc:n-hexane=1:2) to afford 13 (0.19 g). 1H NMR (500 MHz, CDCl3): δ 3.05 (t, J=8.6 Hz, 2H), 4.01 (t, J=8.7 Hz, 2H), 7.46-7.49 (m, 2H), 7.58-7.62 (m, 2H), 7.71 (d, J=8.3 Hz, 1H), 7.75 (d, J=8.3 Hz, 1H), 7.84 (d, J=7.8 Hz, 2H), 9.85 (s, 1H).