Pyridine → 2,2,3,3-Tetrafluorobutane-1,4-diyl bis(trifluoromethanesulfonate)
Reaction equation
[F:1][C:2]([F:10])([C:6]([F:9])([F:8])[CH3:7])[CH:3]([OH:5])O.N1C=CC=CC=1.[F:17][C:18]([F:31])([F:30])[S:19]([O:22]S(C(F)(F)F)(=O)=O)(=[O:21])=[O:20]>ClCCl>[F:8][C:6]([F:9])([C:2]([F:10])([F:1])[CH2:3][O:5][S:19]([C:18]([F:31])([F:30])[F:17])(=[O:21])=[O:20])[CH2:7][O:22][S:19]([C:18]([F:31])([F:30])[F:17])(=[O:20])=[O:21]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a cooled (about 0° C.) solution of 2,2,3,3-tetrafluorobutanediol (15 grams, 93 mmol) and pyridine (19 mL, 230 mmol) in dichloromethane (250 mL), was added dropwise trifluoromethanesulfonic anhydride (34 mL, 200 mmol). After the addition, the mixture was stirred at about 0° C. for about one hour, followed by stirring at room temperature for one additional hour, then diluted with dichloromethane, washed with water and brine, dried over magnesium sulfate, filtered and concentrated to near dryness, leaving a dichloromethane-containing oil. 1H NMR (400 MHz, CDCl3) δ 4.82 (m). 19F NMR (376 MHz, CDCl3) δ−120.83 (m, 4H), −74.38 (s, 6H).
Workup
- additionAfter the addition
- stirringby stirring at room temperature for one additional hour
- washwashed with water and brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customleaving a dichloromethane-
- additioncontaining oil
Sources & evidence
- ORD record
- ord-499e9b7c85144d5b9244dde8fd7f7488
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06812350B2
Reaction notes
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