Methyl 5-formylthiophene-3-carboxylate → Methyl 5-(hydroxymethyl)thiophene-3-carboxylate

To a solution of methyl 5-formylthiophene-3-carboxylate (500 mg) in ethanol (5.9 mL) was added sodium borohydride (55.6 mg) at room temperature in small portions, and the mixture was stirred for one hour. The reaction mixture was concentrated under reduced pressure. A saturated aqueous sodium hydrogen carbonate solution was added to the residue and this resulting mixture was extracted with ethyl acetate. The aqueous layer was extracted once again with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (403 mg).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionA saturated aqueous sodium hydrogen carbonate solution was added to the residue
3. extractionthis resulting mixture was extracted with ethyl acetate
4. extractionThe aqueous layer was extracted once again with ethyl acetate
5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

ORD-Eintrag

ord-3d9e36c27dc548c0b31f822d42cb033c

Quelldatensatz

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08680120B2