反应详情

To an ambient temperature suspension of potassium tert-butoxide (2.05 g, 18.27 mmol) in THF (60 mL) is added the (methoxymethyl)triphenyl phosphonium chloride (6.26 g, 18.27 mmol). The reaction mixture is stirred at room temperature for 20 min. Solid methyl 4-formylbenzoate (1.0 g, 6.09 mmol) is added and the reaction is stirred at room temperature overnight. The reaction mixture is quenched with saturated aq. NH4Cl and concentrated. The residue is partitioned between Et2O and water. The aqueous layer is extracted with Et2O and the combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated, and chromatographed (0% to 30% EtOAC/Hex) to yield the title compound (939 mg, 80%) as a mix of E/Z isomers.

1. stirringthe reaction is stirred at room temperature overnight
2. customThe reaction mixture is quenched with saturated aq. NH4Cl
3. concentrationconcentrated
4. customThe residue is partitioned between Et2O and water
5. extractionThe aqueous layer is extracted with Et2O
6. washthe combined organic layers are washed with brine
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated
10. customchromatographed (0% to 30% EtOAC/Hex)