Ethyl Acetate → (2-Cyclopropyl-6-(trifluoromethyl)pyridin-3-yl)methanol
Reaction equation
[CH:1]1([C:4]2[N:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:5]=2[C:6](OC)=[O:7])[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOC(C)=O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1>[CH:1]1([C:4]2[C:5]([CH2:6][OH:7])=[CH:10][CH:11]=[C:12]([C:14]([F:17])([F:15])[F:16])[N:13]=2)[CH2:3][CH2:2]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of methyl 2-cyclopropyl-6-(trifluoromethyl)nicotinate (1 g, 4.08 mmol) in THF (6 mL) at 0° C. under argon was added 1.0 M lithium aluminum hydride in THF solution (6 mL, 6.0 mmol). The reaction mixture was stirred at 0° C. for 15 min. EtOAc (20 mL) was added to the reaction mixture, which was then stirred at room temperature for 30 min. A 10% aqueous potassium sodium tartrate solution (20 mL) was added to the reaction mixture and stirring was continued for another 30 min. The organic layer was separated, washed with saturated aqueous NaCl, dried (MgSO4), filtered and concentrated to obtain 890 mg of the title compound as a pale yellow oil. HPLC/MS: retention time=3.055 min, [M+H]+=218.
Workup
- stirringwas then stirred at room temperature for 30 min
- stirringstirring
- waitwas continued for another 30 min
- customThe organic layer was separated
- washwashed with saturated aqueous NaCl
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0e3555c68a804dab8810b6c913994195
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07452892B2
Reaction notes
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