Triethylamine → 2-Acetyl-7-methoxyfuro[2,3-c]pyridine
Reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=[C:16]([CH:18]([OH:20])[CH3:19])[O:15][C:14]=12.C(N(CC)CC)C>ClCCl.CS(C)=O.O>[C:18]([C:16]1[O:15][C:14]2=[C:9]([O:8][CH3:7])[N:10]=[CH:11][CH:12]=[C:13]2[CH:17]=1)(=[O:20])[CH3:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of oxalyl chloride (0.97 ml) in dry dichloromethane (10 ml) was stirred at −55° C. under an atmosphere of dry nitrogen. A solution of dimethyl sulfoxide (1.7 ml) in dry dichloromethane (5 ml) was added dropwise and stirring continued for 5 minutes at −55° C. 1-(7-Methoxyfuro[2,3-c]pyridin-2-yl)ethanol (1.9 g) in dimethyl sulfoxide (15 ml) was added dropwise and stirring continued for a further 15 minutes. Triethylamine (6.9 ml) was added and the mixture stirred for a further 5 minutes at −55° C. before warming to room temperature. The mixture was diluted with water (100 ml) and extracted with dichloromethane (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 (1.2 g) as a pale yellow solid.
Workup
- stirringstirring
- waitcontinued for a further 15 minutes
- stirringthe mixture stirred for a further 5 minutes at −55° C.
- extractionextracted with dichloromethane (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-3e9a85aa1c774fc79332cbe677271a64
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06169090A
Reaction notes
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