Acetic Acid → 2-Chloro-6-(trifluoromethyl)pyridine-3-carbaldehyde
Reaction equation
[Cl:1][C:2]1[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#N.CC(C[AlH]CC(C)C)C.C(O)(=[O:25])C.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:25]Participants
6
Conditions
- Temperature
- -78 °C
Procedure
2-Chloro-6-(trifluoromethyl)nicotinonitrile (340 mg, 1.65 mmol) was diluted with toluene (2.0 mL), placed under nitrogen and cooled to −78° C. DIBAL-H (3292 μl, 3.29 mmol) was added dropwise and the reaction was stirred for 1 hour. The reaction was warmed to 0° C. and acetic acid (1 mL) was added followed by 5 mL of water. After stirring for 2 hours, the reaction was extracted twice with ethyl acetate, washed with Rochelle's salt, dried over MgSO4, filtered and concentrated. The material was loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 30% ethyl acetate/hexanes to yield the desired compound (115 mg, 0.549 mmol, 33.3% yield) as a clear oil.
Workup
- temperatureThe reaction was warmed to 0° C.
- stirringAfter stirring for 2 hours
- extractionthe reaction was extracted twice with ethyl acetate
- washwashed with Rochelle's salt
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- washeluted with 5% ethyl acetate/hexanes to 30% ethyl acetate/hexanes
Sources & evidence
- ORD record
- ord-c300dfec95614a06b46a37a9abe342d0
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785445B2
Reaction notes
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