Toluene → HCID 58938005, compound

Participants

Reaction Steps

To a solution of the intermediate from step 3 (2.5 g, 9.5 mmol) in dry CH2Cl2 (320 mL), cooled at −78° C. and under N2 atmosphere, add DIBAL 10M in toluene (28.4 mmol). Allow the mixture to warm to room temperature and stir overnight. Cool the mixture to 0° C. and add AcOH/H2O. Stir at room temperature for 1 hour. Extract the aqueous layer with CH2Cl2 (×2). Combine the organic layers and dry over Na2SO4. Eliminate the solvent and purify by flash chromatography (eluent: EtOAc/hexane 3/1) to obtain the title compound (1.75 g, 69%). 1H-NMR (MeOD, 300 MHz): 9.91 (s, 1H), 7.81-7.73 (m, 4H), 7.37-7.26 (m, 2H), 3.21 (m, 4). 13C-NMR (MeOD, 300 MHz): 193.2, 162.6, 160.3, 134.4, 133.8, 133.2, 131.9, 131.3, 130.6, 128.8, 123.3, 122.4, 32.9, 32.8.

Provenance & Evidence