Acetaldehyde → 1-(7-Methoxyfuro[2,3-c]pyridin-2-yl)ethanol
Reaction equation
[CH3:1][O:2][C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[CH:11]=[CH:10][O:9][C:8]=12.C([Li])CCC.[CH:17](=[O:19])[CH3:18]>O1CCCC1.O>[CH3:1][O:2][C:3]1[N:4]=[CH:5][CH:6]=[C:7]2[CH:11]=[C:10]([CH:17]([OH:19])[CH3:18])[O:9][C:8]=12Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
A solution of 7-methoxyfuro[2,3-c]pyridine (1.5 g) in dry tetrahydrofuran (50 ml) was stirred at −78° C. under dry nitrogen. n-Butyllithium (1.6N solution in hexanes, 6.9 ml) was added dropwise and the resulting solution stirred at −78° C. for 60 minutes. Acetaldehyde (5.7 ml) was added and stirring continued at −78° C. for 90 minutes before warming to room temperature. The mixture was diluted with water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined organic extracts were dried over magnesium sulfate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 50% hexane in ethyl acetate gave the title compound (1.8 g) as a brown oil.
Workup
- stirringstirring
- waitcontinued at −78° C. for 90 minutes
- temperaturebefore warming to room temperature
- extractionextracted with ethyl acetate (3×100 ml)
- dry with materialThe combined organic extracts were dried over magnesium sulfate
- filtrationfiltered
- customthe solvent removed in vacuo
- customPurification by column chromatography on silica eluting with 50% hexane in ethyl acetate
Sources & evidence
- ORD record
- ord-d57333858d4f4d73b5bc620147836aba
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06169090A
Reaction notes
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