Carbon Dioxide → 3-Methoxythiophene-2-carboxylic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:7]=[CH:6][S:5][CH:4]=1.C([Li])CCC.[C:13](=[O:15])=[O:14].Cl>CCOCC>[CH3:1][O:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:13]([OH:15])=[O:14]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 3-methoxythiophene (4.81 g, 42.1 mmol) in ether (20 mL) at -78° C., butyllithium (17 mL, 47.6 mmol) was added. The reaction mixture was stirred at -78° C. for 1 hour, then it was warmed to 0 ° C. for 3 hours. After to recooling -78° C. the reaction mixture was poured into a beaker filled with crushed dry ice (14.5 g) and allowed to stand until the excess dry ice had completely sublimed. Then the reaction mixture was poured into a mixture of ice (10 g) to which conc. HCl (24 mL) had been added. The product was purified by precipitation from ether and filtering (6.42 g, 96%). EI-MS m/z 159 (M+H)+.
Workup
- temperatureit was warmed to 0 ° C. for 3 hours
- additionAfter to recooling -78° C. the reaction mixture was poured into a beaker
- additionhad been added
- customThe product was purified by precipitation from ether
- filtrationfiltering (6.42 g, 96%)
Sources & evidence
- ORD record
- ord-98169a1de37c4a62bcdac06b8a931f31
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05886044
Reaction notes
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