Acetic Acid → Methyl 2-isocyano-2-(2-thienylmethyl)butyrate
Reaction equation
CC(C)([O-])C.[K+].[N+:7]([CH:9]([CH2:14][CH3:15])[C:10]([O:12][CH3:13])=[O:11])#[C-:8].Br[CH2:17][C:18]1[S:19][CH:20]=[CH:21][CH:22]=1.C(O)(=O)C>O1CCCC1>[N+:7]([C:9]([CH2:17][C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)([CH2:14][CH3:15])[C:10]([O:12][CH3:13])=[O:11])#[C-:8]Participants
Conditions
- Temperature
- -30 °C
Procedure
A suspension of potassium tert.-butoxide (5.5 g) in tetrahydrofuran (50 ml) is cooled to -30° C., and a solution of methyl 2-isocyanobutyrate (5.5 g) in tetrahydrofuran (10 ml) is added dropwise to the suspension at -30° C. The mixture is stirred at the same temperature for 30 minutes and a solution of 2-bromomethylthiophene (6.9 g) in tetrahydrafuran (10 ml) is added dropwise to the mixture. The mixture is stirred at room temperature for 4 hours, adjusted to pH 7 with acetic acid and then concentrated under reduced pressure to remove solvent. The residue is dissolved in a mixture of ethyl acetate and water and the organic layer is collected therefrom. The organic layer is washed with an aqueous saturated sodium chloride solution, dried and concentrated to remove solvent. The residue is distilled under reduced pressure, whereby methyl 2-isocyano-2-(2-thienylmethyl)butyrate (7.7 g) is obtained as pale yellow oil.
Workup
- stirringThe mixture is stirred at room temperature for 4 hours
- concentrationconcentrated under reduced pressure
- customto remove solvent
- dissolutionThe residue is dissolved in a mixture of ethyl acetate and water
- customthe organic layer is collected
- washThe organic layer is washed with an aqueous saturated sodium chloride solution
- customdried
- concentrationconcentrated
- customto remove solvent
- distillationThe residue is distilled under reduced pressure
Sources & evidence
- ORD record
- ord-759e756f67714c06833db969e245f1ad
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04857543
Reaction notes
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