Acetaldehyde → 1-(3-Methylpyridin-2-yl)ethanol
Reaction equation
CN(C)[CH2:3][CH2:4][OH:5].C([Li])CCC.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=1.C(=O)C>CCCCCC.O>[CH3:18][C:14]1[C:13]([CH:4]([OH:5])[CH3:3])=[N:12][CH:17]=[CH:16][CH:15]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
Dissolve N,N-dimethylethanolamine (70.45 mmol) in hexane (90 mL) at 0° C., add 2.5M n-butyl lithium in hexane (140.9 mmol,) and stir for 30 min at this temperature. Add a solution of 3-picoline (35.23 mmol) in hexane (10 mL) and continue stirring at 0° C. for 1 h. Cool the resulting mixture to −78° C., add acetaldehyde (70.45 mmol) and continue stirring at −78° C. for 1 h. Dilute with water, warm to ambient temperature, extract three times with EtOAc, dry over anhydrous Na2SO4, and concentrate in vacuo. Purify by chromatography eluting with hexane/EtOAc (85:15) to give the desired intermediate as a light yellow oil.
Workup
- stirringcontinue stirring at 0° C. for 1 h
- stirringcontinue stirring at −78° C. for 1 h
- temperaturewarm to ambient temperature
- extractionextract three times with EtOAc
- dry with materialdry over anhydrous Na2SO4
- concentrationconcentrate in vacuo
- customPurify by chromatography
- washeluting with hexane/EtOAc (85:15)
Sources & evidence
- ORD record
- ord-4c966a7f9fec4c3f9c12086d811fa25a
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08022062B2
Reaction notes
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