Sodium borohydride → 2,2-Difluoro-2-(pyridin-2-YL)ethanol
Reaction equation
C([O:3][C:4](=O)[C:5]([F:13])([F:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)C.[BH4-].[Na+]>C(O)C>[F:13][C:5]([F:12])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[CH2:4][OH:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To the solution of difluoro-pyridin-2-yl-acetic acid ethyl ester (example 59a, 10 g, 50 mmol) in ethanol (100 mL) was added sodium borohydride (2 g, 52.5 mmol) in 5 portions at 0° C. After stirring at 0° C. for 1 h and room temperature for 1.5 h, the reaction was quenched by slow addition of hydrochloric acid (2 N) at 0° C. The pH was adjusted to 8.5 with 4N NaOH. The product was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The product was crystallized with heptane afforded 2,2-difluoro-2-pyridin-2-yl-ethanol (6.7 g, 84%) as a white solid.
Workup
- customthe reaction was quenched by slow addition of hydrochloric acid (2 N) at 0° C
- extractionThe product was extracted with ethyl acetate
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe product was crystallized with heptane
Sources & evidence
- ORD record
- ord-a0dce31dbe9c4b7f9d06e784e795fdc7
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07326786B2
Reaction notes
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