Hydrochloric Acid → 2,2,2-Trifluoro-1-(pyridin-2-yl)ethan-1-ol
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[O:8].[F:9][C:10]([Si](C)(C)C)([F:12])[F:11].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>C1COCC1.[OH-].[Na+]>[OH:8][CH:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:10]([F:12])([F:11])[F:9]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 2-pyridine carboxaldehyde (2.09 g, 19.5 mmol) and (trifluoromethyl)trimethylsilane (3.33 g, 23.4 mmol) in THF (30 mL) at 0° C. add 1M tetrabutylammonium fluoride in THF (956 μl, 0.956 mmol). Continue stirring for 30 min at 0° C. and then at ambient temperature for 2 h. Add 1M aqueous HCl (20 mL) and stir 2 h at ambient temperature. Dilute with aqueous 1M aqueous NaOH to pH 8, extract the mixture three times with EtOAc, dry over anhydrous Na2SO4, and concentrate in vacuo. Purify by chromatography eluting with hexane/EtOAc (8:2) to give the desired intermediate as a yellow oil (3.22 g, 93%).
Workup
- waitat ambient temperature for 2 h
- stirringstir 2 h at ambient temperature
- extractionextract the mixture three times with EtOAc
- dry with materialdry over anhydrous Na2SO4
- concentrationconcentrate in vacuo
- customPurify by chromatography
- washeluting with hexane/EtOAc (8:2)
Sources & evidence
- ORD record
- ord-b33d811f9a2249cd8ee36f2a0da13f6f
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08580780B2
Reaction notes
Loading…