Carbon Dioxide → 5-Acetylthiophene-2-carboxylic acid
Reaction equation
[CH3:1][C:2]1([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)OCC[O:3]1.CN(C)CCN(C)C.C([Li])CCC.[C:25](=[O:27])=[O:26]>O1CCCC1>[C:2]([C:7]1[S:8][C:9]([C:25]([OH:27])=[O:26])=[CH:10][CH:11]=1)(=[O:3])[CH3:1]Participants
Conditions
- Temperature
- -78 °C
Procedure
2-Methyl-2-(2-thienyl)-1,3-dioxolan (6.6 g) (synthesized in accordance with the method described in Tetrahedron, 41, 3803 (1985)) was dissolved in tetrahydrofuran (200 ml), and N,N,N', N'-tetramethylethylenediamine (5.87 ml) was added. The mixture was cooled to -78° C., and n-butyllithium (1.6M in hexane, 25 ml) was slowly added dropwise. The mixture was stirred at the same temperature for 2 hours, and warmed slowly to room temperature for a period of 2 hours with introducing carbon dioxide gas. The reaction mixture was concentrated under reduced pressure, and 2N hydrochloric acid (200 ml) was added. The mixture was stirred for 3 hours, and precipitated crystals were collected by filtration, washed with water and dried to give 5-acetyl-2-thiophenecarboxylic acid (3.87 g) as crystals.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure, and 2N hydrochloric acid (200 ml)
- additionwas added
- stirringThe mixture was stirred for 3 hours
- customprecipitated crystals
- filtrationwere collected by filtration
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-792bdbe742b94e23bd6aaa41ef59705d
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05840917
Reaction notes
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