Reaction #220642

Reaction equation

hydrochloric acid

3-(3-bromophenyl)-4-(5-chloro-2-pyridyl)-2-butanone

3-(3-Bromophenyl)-4-(5-chloro-2-pyridyl)-2-butanone

lithium tri(sec-butyl)borohydride

→

title compound

3-(3-Bromophenyl)-4-(5-chloro-2-pyridyl)-2-butanol

Solvents

THF

Conditions

Workup

1. 1
   TemperatureThe reaction was cooled to 0° C.
2. 2
   Otherthe resulting mixture was partitioned between hexane (200 mL) and water (200 mL)
3. 3
   OtherThe aqueous layer was separated
4. 4
   Extractionthe organic layer extracted with 2 M hydrochloric acid (2×100 mL)
5. 5
   Extractionwas extracted with EtOAc (2×200 mL)
6. 6
   DryingThe combined extracts were dried over anhydrous sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated to dryness

Procedure

To a solution of 3-(3-bromophenyl)-4-(5-chloro-2-pyridyl)-2-butanone (Step B, 6.7 g, 20 mmol) in 50 mL anhydrous THF at −78° C. was added lithium tri(sec-butyl)borohydride (1.0 M in THF, 30 mL, 30 mmol), and the reaction was allowed to warm to room temperature overnight. The reaction was cooled to 0° C., and was carefully added 2 M hydrochloric acid (50 mL), and the resulting mixture was partitioned between hexane (200 mL) and water (200 mL). The aqueous layer was separated and the organic layer extracted with 2 M hydrochloric acid (2×100 mL). The combined aqueous extracts were neutralized with 5 N aqueous sodium hydroxide (pH>12), and was extracted with EtOAc (2×200 mL). The combined extracts were dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to afford the title compound.

Source