ChemicalBook CAS DataBase List 2-PHENYL-2,3-DIHYDRO-PYRAN-4-ONE

2-PHENYL-2,3-DIHYDRO-PYRAN-4-ONE synthesis

9synthesis methods

Product Name:2-PHENYL-2,3-DIHYDRO-PYRAN-4-ONE
CAS Number:40989-96-6
Molecular formula:C11H10O2
Molecular Weight:174.2

1-METHOXY-3-TRIMETHYLSILOXY-1,3-BUTADIENE

59414-23-2
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100-52-7 Synthesis

100-52-7
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40989-96-6
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Yield:40989-96-6 73%

Reaction Conditions:

with zinc(II) chloride in tetrahydrofuran;diethyl ether at 20;Inert atmosphere;Diels-Alder Cycloaddition;

Steps:

3.2. General Procedure for the Synthesis of Racemic Dihydropyranones

To a flame dried flask under an atmosphere of argon was added ZnCl₂ (39 mg, 0.28 mmol, 3 mol %) and anhydrous diethyl ether (0.4 mL, 3 mol %). Anhydrous THF (100 mL) was added followed by freshly-purified aldehyde (9.42 mmol, 1.0 eq). The reaction was stirred for 10 min before dropwise addition of Danishefsky’s Diene (1) (2.7 mL, 14.13 mmol, 1.5 eq). The reaction was stirred overnight at room temperature and then filtered through celite and concentrated. The crude product was purified by flash column chromatography to afford the respective dihydropyranones.

References:

Edwards, Hannah J.;Goggins, Sean;Frost, Christopher G. [Molecules,2015,vol. 20,# 4,p. 6153 - 6166]

54125-02-9 Synthesis