Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[CH3:14][C:15]([CH3:20])([CH2:18][CH3:19])[CH2:16][OH:17].ClCCl.Cl>C(OCC)(=O)C.N1C=CC=CC=1>[N+:11]([C:8]1[CH:7]=[CH:6][C:5]([O:4][C:2](=[O:3])[O:17][CH2:16][C:15]([CH3:20])([CH3:14])[CH2:18][CH3:19])=[CH:10][CH:9]=1)([O-:13])=[O:12]
To a mixture of 4-nitrophenyl chloroformate (1.97 g), 2,2-dimethylbutan-1-ol [CAS No. 1185-33-7] (1 g), and dichloromethane (30 mL), pyridine (1.58 mL) was added, and the resulting mixture was stirred at room temperature for 3 days. To the mixture, ethyl acetate and 1 N hydrochloric acid were added. After shaking the resulting mixture, the organic layer was collected, sequentially washed twice with water and with saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The desiccant was filtered off, and the filtrate obtained was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (mixed solvent of heptane-ethyl acetate) to obtain the captioned compound (2.23 g).
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