Ethyl Acetate → (2-Methyl-6-(trifluoromethyl)pyridin-3-yl)methanol

HRID 271455Notes

Reaction equation

HRID 271455 reaction equation
[CH3:1][C:2]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].CCOC(C)=O>C1COCC1.O>[CH3:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:8][CH:9]=[C:10]([C:12]([F:14])([F:13])[F:15])[N:11]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 9357Potassium Sodium TartrateHCID 2779428Methyl 2-methyl-6-(trifluoromethyl)nicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2760122(2-Methyl-6-(trifluoromethyl)pyridin-3-yl)methanolYield 98.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To the solution of methyl 2-methyl-6-(trifluoromethyl)nicotinate (8.8 g, 40 mmol) in 40 mL dry THF at 0° C. under argon was added 1.0 M lithium aluminum hydride in THF solution (40 mL, 40 mmol) drop-wise over 15 min. The reaction mixture was allowed to warm to room temperature over 1 h. HPLC/MS analysis indicated that the reaction was complete. Rochelle's salt, 10% aqueous solution (20 mL) was carefully added to the stirring reaction mixture over a period of 10 min. After 1 h of subsequent stirring, 50 mL EtOAc and water were added. The layers were separated. The organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to obtain 7.5 g of the title compound as a colorless oil, which was greater than 98% pure. HPLC/MS: retention time=2.1 min, [M+H]30 =192.

Workup

  1. customThe layers were separated
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e8edef4ea77542828c1f80b53c910184
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

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