2,6-Lutidine → 3-Fluoropropyl trifluoromethanesulfonate

To a cold (−25° C.), stirred solution of 2,6-Lutidine (4.60 mL, 39.5 mmoL) in DCM (30 mL) was added triflic anhydride (6.00 mL, 35.5 mmoL) over 3 min. Then 3-fluoropropane-1-ol (1.61 g, 20.6 mmoL) was added. The reaction mixture was warmed to room temperature for 2.5 h. The reaction mixture was then concentrated to half its volume and purified by flash chromatography (Teledyne ISCO CombiFlash, isocratic DCM, REDISEP® SiO2 120 g, detecting at 254 nM, and monitoring at 220 nM). Concentration of the appropriate fractions provided Intermediate S-4A (2.92 g, 67.4%). 1H NMR (400 MHz, chloroform-d) δ ppm 4.69 (2H, t, J=6.16 Hz), 4.65 (1H, t, J=5.50 Hz), 4.54 (1H, t, J=5.61 Hz), 2.25 (1H, dt, J=11.39, 5.86 Hz), 2.19 (1H, dt, J=11.44, 5.94 Hz)

1. concentrationThe reaction mixture was then concentrated to half its volume
2. custompurified by flash chromatography (Teledyne ISCO CombiFlash, isocratic DCM, REDISEP® SiO2 120 g, detecting at 254 nM, and monitoring at 220 nM)
3. customConcentration of the appropriate fractions provided Intermediate S-4A (2.92 g, 67.4%)

ORD-Eintrag

ord-5cc680f4e9cc44fa84c60879d1b8e6f5

Quelldatensatz

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09249157B2