Ethyl 5-fluoropyridine-2-carboxylate → 5-Fluoropyridine-2-carboxaldehyde

To a solution of ethyl 5-fluoropyridine-2-carboxylate (25 g, 148 mmol) in tetrahydrofuran (250 mL) at −78° C. was added dropwise diisobutylaluminum hydride (1.0 M in hexanes; 296 mL, 296 mmol). After 1 h, the reaction was quenched with ethyl alcohol (10 mL). Saturated aqueous sodium potassium tartrate tetrahydrate (1.3 L) was added and the aqueous layer was extracted with ethyl acetate (2×). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered. The solution mixture (1.4 L) was carried onto the next step without concentration. MS 125.9 (M+1).

1. customthe reaction was quenched with ethyl alcohol (10 mL)
2. additionSaturated aqueous sodium potassium tartrate tetrahydrate (1.3 L) was added
3. extractionthe aqueous layer was extracted with ethyl acetate (2×)
4. washThe combined organic extracts were washed with brine
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationThe solution mixture (1.4 L) was carried onto the next step without concentration

ORD record

ord-25ac5cddd6394cc69dbf8364ca6c899d

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247401B2