Water → 2-(1-Phenylthiocycloprop-1-yl)oxy-5-(trifluoromethoxy)benzenemethanol

Participants

Reaction Conditions

Reaction Steps

Silver carbonate (4.82 g, 17.5 mmol) was added to a solution of 2-hydroxy-5-(trifluoromethoxy)benzaldehyde (2.0 g, 9.7 mmol) and (1-iodocycloprop-1-yl)phenylsulfide (Cohen T. and Matz J. R., J. Am. Chem. Soc. 1980, 102, 6902) (5.48 g, 17.5 mmol) in toluene (25 mL) and the mixture was stirred at 40° C. for 36 h., then at room temperature for 16 h. The mixture was diluted with ethyl acetate and filtered, washing well with ethyl acetate. The mixture was washed with aqueous sodium hydroxide (1M, 6×75 mL) and brine (75 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was dissolved in ethanol, (15 mL), cooled to 0° C. and sodium borohydride, (0.74 g, 19.6 mmol), was added. The mixture was stirred at room temperature for 1 h., poured into water and extracted into ethyl acetate (3×100 mL). The combined organic fractions were dried (MgSO4), and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/EtOAc (97:3 increasing to 70:30), to give the title compound as a yellow oil (1.8 g, 53%). 1H NMR (250 MHz, CDCl3) 1.41-1.44 (2H, m), 1.46-1.51 (2H, m), 1.84 (1H, t, J 6.5 Hz), 4.58 (2H, d, J 6.5 Hz), and 7.18-7.48 (8H, m).

Provenance & Evidence