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-7f12c2c20c834b1db905bf159aa9d75d

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08461185B2