Methoxymethyl-triphenylphosphonium chloride → HCID 67342613, compound

Participants

Reaction Steps

To a an ambient temperature suspension of potassium tert-butoxide (419 mg, 3.73 mmol) in THF (20 mL) is added (methoxymethyl)triphenylphosphonium chloride (1.28 g, 3.73 mmol) and is stirred at room temperature for 30 min. 3-Fluoro-4′-trifluoromethyl-biphenyl-4-carbaldehyde (500 mg, 1.87 mmol) is added and the reaction mixture continues to stir at room temperature. After 2 h TLC (30% EtOAc/hexane) indicates complete consumption of starting material. The reaction is quenched with saturated aqueous NH4Cl and concentrated. The residue is partitioned between EtOAc (50 mL) and water (20 mL). The aqueous layer is extracted with EtOAc (50 mL) and the combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated and chromatographed (120 g SiO2, 5% EtOAc/Hexanes) to yield the title compound (474 mg, 85%).

Provenance & Evidence