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 기록

ord-08a56339788949eca26e79a54124085f

출처 데이터셋

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08507682B2