Acetone → 3-Fluoro-α,α-dimethyl-4-pyridinemethanol

3-Fluoropyridine (11.0 g, 113.0 mmol) in 100 mL of THF was treated with LDA (1.5M, 100.0 mL, 150.0 mmol) at −78° C. for 50 min under argon. Acetone (28 mL) was added and the resulting reaction mixture was stirred at −78° C. to −40° C. for 50 min. The reaction was then quenched with aqueous NH4Cl and extracted with ether. The combined organic layers were washed with H2O and brine, then dried over Na2SO4 and concentrated under vacuum. Purification by MPLC (80 g column, 0 to 40% ethyl acetate in hexane as eluant) afforded the title compound. Spectroscopic data: 1H-NMR (300 MHz, CDCl3): δ ppm 1.65 (s, 6 H), 7.27 (dd, J=5.57 Hz, 1 H), 8.36-8.39 (m, 2 H).

1. customthe resulting reaction mixture
2. customThe reaction was then quenched with aqueous NH4Cl
3. extractionextracted with ether
4. washThe combined organic layers were washed with H2O and brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated under vacuum
7. customPurification by MPLC (80 g column, 0 to 40% ethyl acetate in hexane as eluant)

ORD-Eintrag

ord-0b1a3deffe2544b0bbea81136c189aaa

Quelldatensatz

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08703797B2