Pyridine → 3-Chloro-2-formyl-5-(tetrahydro-2H-pyran-2-yloxy)phenyl trifluoromethanesulfonate
Reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([OH:10])[CH:5]=[C:4]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:3]=1.N1C=CC=CC=1.[O:24](S(C(F)(F)F)(=O)=O)[S:25]([C:28]([F:31])([F:30])[F:29])(=O)=[O:26]>C(Cl)Cl>[F:29][C:28]([F:31])([F:30])[S:25]([O:10][C:6]1[CH:5]=[C:4]([O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:3]=[C:2]([Cl:1])[C:7]=1[CH:8]=[O:9])(=[O:26])=[O:24]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of 6-chloro-2-hydroxy-4-(tetrahydro-pyran-2-yloxy)benzaldehyde (10.5 g, 40.9 mmol) and pyridine (14.6 mL, 0.20 mol) in DCM (150 mL) cooled at −10˜0° C. was added Tf2O (10.3 mL, 61.2 mmol) dropwise. The reaction mixture was stirred at 0° C. for an additional 2 h and quenched with cold brine (40 mL). The resulting mixture was extracted with EtOAc (2×50 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (EtOAc: PE=1:200) to give the title compound as a yellow oil (10.5 g. Yield: 66%).
Workup
- temperaturecooled at −10˜0° C.
- customquenched with cold brine (40 mL)
- extractionThe resulting mixture was extracted with EtOAc (2×50 mL)
- dry with materialThe combined organic layers were dried over anhydrous Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography on silica gel (EtOAc: PE=1:200)
Sources & evidence
- ORD record
- ord-2c912b965cff4bd48abe9de1a867b6cc
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08343944B2
Reaction notes
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