Phenoxyacetaldehyde → 2-Phenoxymethyl-2,3-dihydropyran-4-one

Temperatur

-5 °C

1-Methoxy-3-(trimethylsilyloxy)-1,3-butadiene (4.95 ml; 26 mmol) was added to a solution of phenoxyacetaldehyde (3.56 g, 26 mmol) in DCM (40 ml). The solution was cooled to −5° C. A 2.3 M solution of zinc chloride in DCM (5.6 ml, 13 mmol) was added. The reaction mixture was stirred for 16 hours, while it was warming up to room temperature. It was diluted with ethyl acetate (150 ml) and washed with a 10% aqueous solution of sodium hydrogensulphate (100 ml). The aqueous phase was extracted with ethyl acetate (100 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (100 ml) and dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (200 g), using ethyl acetate/heptane (1:1) as eluent, to give 2.36 g of 2-phenoxymethyl-2,3-dihydropyran-4-one.

1. temperaturewas warming up to room temperature
2. washwashed with a 10% aqueous solution of sodium hydrogensulphate (100 ml)
3. extractionThe aqueous phase was extracted with ethyl acetate (100 ml)
4. washThe combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (100 ml)
5. dry with materialdried over magnesium sulphate
6. customThe solvent was removed in vacuo
7. customThe crude product was purified by flash chromatography on silica (200 g)

ORD-Eintrag

ord-accf40c1ec45459c972fdbb8ac03c32c

Quelldatensatz

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06610721B2