Tetrahydrofuran → 4-((4-Fluorophenyl)(hydroxy)methyl)benzaldehyde

Participants

Reaction Steps

To a stirred solution of terepathaldehyde (0.5 g, 3.7 mmol) in anhydrous THF (8 ml) at 0° C. was added 2M THF solution of 4-fluorophenyl magnesium bromide (1.86 ml; 3.72 mmol) drop wise and the mixture was allowed to warm up to room temperature and stirred for 4 h. The mixture was then quenched with NH4Cl solution and diluted with to 100 ml with EtOAc. The organic layer was washed with H2O, dried over MgSO4, filtered and the filtrate evaporated to dryness. The residue was purified by FCC (SiO2) to give the desired product (0.23 g; 27%) as creamy paste. 1H-NMR (CDCl3) 2.57 (s, 1H); 5.86 (s, 1H); 7.0 (tr, 2H, J=8.58 Hz); 7.28-7.33 (m, 2H); 7.51 (d, 2H, J=7.98 Hz); 7.81 (d, 2H, J=8.1 Hz); 9.95 (s, 1H).

Provenance & Evidence