Citric Acid → 2-(1,3-Dioxolan-2-yl)-1,3-thiazole-5-carbaldehyde

Temperatur

-70 °C

To a solution of 2-(1,3-dioxolan-2-yl)-1,3-thiazole (10.00 g) in tetrahydrofuran (150 mL) was slowly added a 1.6M n-butyllithium hexane solution (44 mL) at −70° C. under a nitrogen atmosphere. The reaction mixture was stirred at −70° C. for 1 hr and N,N-dimethylformamide (14 g) was added. The reaction mixture was warmed to room temperature, 10% aqueous citric acid solution was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (6.64 g, yield 56%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (3:2, volume ratio). MS: 186 (MH+).

1. temperatureThe reaction mixture was warmed to room temperature
2. extractionthe mixture was extracted with ethyl acetate
3. washThe ethyl acetate layer was washed with saturated brine
4. dry with materialdried (MgSO4)
5. concentrationconcentrated

ORD-Eintrag

ord-c289bddec93b4a229f84f7c1dc478c1c

Quelldatensatz

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08318746B2