2-Fluoro-5-formylpyridine → 1-(6-Fluoropyridin-3-yl)ethan-1-ol

A solution of 6-fluoronicotinaldehyde (1.12 g, 8.95 mmol, Frontier Scientific, Cat#: F1911, Batch#: RP09-2154) in THF (11.0 mL) was treated dropwise with methylmagnesium bromide (1.4 M solution in PhMe/THF (75:25), 7.03 mL, 9.85 mmol, Aldrich) and allowed to stir at RT for 20 min. The reaction mixture was quenched by the addition of a saturated solution of NH4Cl (aq.) and allowed to stir for 10 min. The reaction mixture was extracted with EtOAc (2×60 mL), dried over MgSO4, filtered and concentrated. Purification on the ISCO (12 g column, 25-70% EtOAc in hexanes) gave the title compound (1.05 g, 83% yield) as a pale yellow viscous oil. 1H NMR (400 MHz, CDCl3) δ 8.20 (d, J=2.0Hz, 1H); 7.85 (td, J=8.1, 2.5 Hz, 1H); 6.93 (dd, J=8.4, 2.9 Hz, 1H); 4.98 (qd, J=6.5, 3.9 Hz, 1H); 1.53 (d, J=6.5 Hz, 3H). m/z (ESI, +ve) 142.1 (M+H)+.

1. customThe reaction mixture was quenched by the addition of a saturated solution of NH4Cl (aq.)
2. stirringto stir for 10 min
3. extractionThe reaction mixture was extracted with EtOAc (2×60 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customPurification on the ISCO (12 g column, 25-70% EtOAc in hexanes)

ORD record

ord-6db894993cd54d2989760404bed6a6d9

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772480B2