Sodium borohydride → (6-Tert-butylpyridin-3-yl)methanol
Reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CCO>[C:1]([C:5]1[N:6]=[CH:7][C:8]([CH2:9][OH:10])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
6-tert-Butylnicotinaldehyde (363.0 mg, 2.22 mmol) was dissolved in EtOH (20 ml). NaBH4 (193.5 mg, 5.12 mmol) was added. The mixture was stirred at r.t. for 1.0 h. The solvent was removed under reduced pressure. The residue was suspended in aqueous Na2CO3 and the product extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated yielding 311.5 mg the title compound as a colourless oil (85%).
Workup
- customThe solvent was removed under reduced pressure
- extractionthe product extracted with EtOAc
- dry with materialThe combined organic extracts were dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-257130de09d74c91acb505135728ec3c
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415333B2
Reaction notes
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