2,6-Lutidine → 3,3,3-Trifluoropropyl trifluoromethanesulfonate

To a cold (−25° C.), stirred solution of 2,6-lutidine (18.38 mL, 158 mmol) in CH2Cl2 (120 mL) was added Tf2O (24.88 mL, 147 mmol) over 3 min, and stirred for 5 min. To the reaction mixture was added 3,3,3-trifluoropropan-1-ol (12 g, 105 mmol) over an interval of 3 min. After 2 hr, the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction mixture was concentrated to half volume, then purified by loading directly on silica gel column (330 g ISCO) and eluted with CH2Cl2. Obtained Preparation 1M (13.74 g, 53%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 4.71 (2H, t, J=6.15 Hz), 2.49-2.86 (2H, m).

1. waitAfter 2 hr
2. stirringstirred for 1 hr
3. concentrationThe reaction mixture was concentrated to half volume
4. custompurified
5. washeluted with CH2Cl2
6. customObtained
7. customPreparation 1M (13.74 g, 53%) as a colorless oil

ORDレコード

ord-9b193238fec8414dbb1c1a46e35a7a20

出典データセット

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08822454B2