Methoxymethyl-triphenylphosphonium chloride → 4-(2-Methoxy-1-methyl-vinyl)-3-methyl-4'-trifluoromethyl-biphenyl

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Reaction Steps

To a an ambient temperature suspension of potassium tert-butoxide (2.42 g, 21.56 mmol) in THF (70 mL) is added (methoxymethyl)triphenylphosphonium chloride (7.39 g, 21.56 mmol) and is stirred at room temperature for 30 min. 1-(3-methyl-4′-trifluoromethyl-biphenyl-4-yl)-ethanone (2.0 g, 7.19 mmol) is added and the reaction mixture continues to stir at room temperature. After 2 h TLC (20% EtOAc/hexane) indicates complete consumption of starting material. The reaction is quenched with saturated aqueous NH4Cl and concentrated. The residue is partitioned between EtOAc (100 mL) and water (30 mL). The aqueous layer is extracted with EtOAc (100 mL) and The combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated and chromatographed (120 g SiO2, 10% EtOAc/Hexanes) to yield the title compound (2.22 g, quant.).

Provenance & Evidence