Sodium borohydride → (4-((6-Chloropyridin-3-yl)oxy)-3-fluorophenyl)methanol
Reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=2[F:17])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][C:10]=2[F:17])=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 4-((6-chloropyridin-3-yl)oxy)-3-fluorobenzaldehyde (2.80 g, 11.1 mmol) in methanol (25 mL) was added portionwise solid NaBH4 (0.842 g, 22.3 mmol) at room temperature. The reaction mixture was stirred at 25° C. for 2 h, concentrated to remove solvent, dissolved in water (50 mL) and extracted with ethyl acetate (50 mL×2). Combined organic parts were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The crude was used into next step without purification (2.8 g).
Workup
- concentrationconcentrated
- customto remove solvent
- dissolutiondissolved in water (50 mL)
- extractionextracted with ethyl acetate (50 mL×2)
- washCombined organic parts were washed with brine
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude was used into next step without purification (2.8 g)
Sources & evidence
- ORD record
- ord-b27902b7a0314f36aa75815c99f5066a
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09051325B2
Reaction notes
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