HCID 57608496, compound → HCID 90444194, compound
Reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[OH:12][CH:13]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([I:30])[CH:25]=1)[CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20]>C(Cl)Cl>[I:30][C:26]1[CH:25]=[C:24]([C:13](=[O:12])[CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH:29]=[CH:28][CH:27]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Molecular sieves (20.0 g) and PCC (28.0 g, 127 mmol) were added portionwise to a stirred solution of tert-butyl (3-hydroxy-3-(3-iodophenyl)propyl)carbamate (16) (40.0 g, 106 mmol) in anhydrous CH2Cl2 (500 mL) under argon atmosphere at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 20 min. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in water (300 mL), extracted with EtOAc (2×300 mL), washed with brine (300 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (100-200 silica mesh, 15-20% EtOAc-hexane) gave tert-butyl (3-(3-iodophenyl)-3-oxopropyl)carbamate (17) as a pale yellow oil. Yield (21.0 g, 54%); 1H NMR (400 MHz, CDCl3) δ 8.27 (s, 1H), 7.95-7.91 (m, 2H), 7.21 (t, J=8.0 Hz, 1H), 3.57-3.51 (m, 2H), 3.18-3.12 (m, 2H), 1.83-1.76 (m, 1H), 1.45 (s, 9H); MS: m/z 378.12 [M+H]+.