Acetic Acid → Pivalaldehyde
Reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:3]=1[CH:4]([OH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[C:17](O)(=O)C>>[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:3]=1[CH:4]([OH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[CH3:2][C:3]([CH3:12])([CH3:17])[CH:4]=[O:11]Participants
4
Procedure
In 20 ml of acetic acid was dissolved 2.0 g of 2-amino-5-bromo-α-(2-pyridyl)benzyl alcohol obtained in (1) together with 0.86 ml of trimethylacetoaldehyde. To the solution was added 0.36 g of sodium borohydride under ice-cooling. The reaction mixture was stirred for 30 minutes at room temperature and then subjected to extraction with a mixture of 100 ml of water and 150 ml of ethyl acetate. The ethyl acetate layer was washed with 1N sodium hydroxide, dried over anhydrous magnesium sulfate, and concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=5:1) to afford 5-bromo-2-neopentylamino-α-(2-pyridyl)benzyl alcohol (2.4 g) as am oily product.
Sources & evidence
- ORD record
- ord-414e65b896b74b0c839299592c104072
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05885979
Reaction notes
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