tert-Butyl (4-(hydroxymethyl)-2-methoxyphenyl)carbamate → Tert-butyl 4-formyl-2-methoxyphenylcarbamate
Reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[OH:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[C:16]([O:28][CH3:29])[CH:15]=1>ClCCl>[CH:13]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[C:16]([O:28][CH3:29])[CH:15]=1)=[O:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred suspension of finely ground PCC (80 mg, 0.56 mmol) and Celite (80 mg) in dry dichloromethane (2 ml) at room temperature was added drop wise a solution of the alcohol 8 (92.9 mg, 0.37 mmol) in dichloromethane (1 ml followed by 0.7 ml rinse). The mixture was stirred in the dark for 20 minutes. The reaction mixture was adsorbed on silica gel and purified by normal phase MPLC, eluting with hexanes/ethyl acetate 20-40% gradient. GC-MS EI+: m/z 251 (M+); LC-MS ESI+: m/z 252 (M+H+). Yield: 72.7 mg (78%). H-NMR (400 MHz, CD2Cl2): 9.06 (1H, brs) 8.02 (1H, d, J=8 Hz) 7.65 (1H, s) 6.92 (1H, dd, J=8 Hz, 0.4 Hz) 4.67 (1H, s) 1.22 (9H, s).