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

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.).

1. stirringto stir at room temperature
2. customconsumption of starting material
3. customThe reaction is quenched with saturated aqueous NH4Cl
4. concentrationconcentrated
5. customThe residue is partitioned between EtOAc (100 mL) and water (30 mL)
6. extractionThe aqueous layer is extracted with EtOAc (100 mL)
7. washThe combined organic layers are washed with brine
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customchromatographed (120 g SiO2, 10% EtOAc/Hexanes)

ORD-Eintrag

ord-77c2072cf17744559b475ccbdb1c0169

Quelldatensatz

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07989457B2