Reaction #324436

Reaction equation

LiBH4

ethyl chloroformate

6-trifluoromethyl-pyridine-2-carboxylic acid

triethylamine

→

title compound

(6-Trifluoromethyl-pyridin-2-yl)-methanol

Solvents

THF

Conditions

Workup

1. 1
   workup.WAITAfter an additional 30 min
2. 2
   Otherthe ice bath was removed
3. 3
   workup.WAITAfter 1 h
4. 4
   Otherquenched with MeOH
5. 5
   Extractionthe mixture extracted with EtOAc (2×)
6. 6
   OtherThe combined organic fractions were dried

Procedure

To a solution of 6-trifluoromethyl-pyridine-2-carboxylic acid (500 mg, 3 mmol) in dry THF at 0° C., was added triethylamine (0.36 mL, 2.6 mmol) followed by ethyl chloroformate (0.25 mL, 2.6 mmol). After 30 min, LiBH4 (2 M in THF, 3.3 mL, 6.5 mmol) was added. After an additional 30 min, the ice bath was removed. After 1 h, the reaction was cooled to 0° C. and quenched with MeOH followed by 1N NaOH and EtOAc. The pH of the solution was adjusted to pH=5 with 1N HCl and the mixture extracted with EtOAc (2×). The combined organic fractions were dried to provide the title compound that was used without further purification. 1H NMR (CDCl3): 7.89 (dd, J=7.8, 7.8 Hz, 1H), 7.61 (d, J=7.7 Hz, 1H), 7.51 (d, J=7.9 Hz, 1H), 4.85 (s, 2H).

Source