Acetonitrile → 3-Hydroxy-5-methoxythiophene-2-carbonitrile
Reaction equation
C(O[C:4]([CH2:6][C:7]([O:9][CH3:10])=[S:8])=[O:5])C.[C:11](#[N:13])[CH3:12].C[O-].[Na+]>CO>[C:11]([C:12]1[S:8][C:7]([O:9][CH3:10])=[CH:6][C:4]=1[OH:5])#[N:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
81 g of O-methyl 2-ethoxycarbonyl-thioacetate and then 38 g of acetonitrile were added to a solution of 27 g of sodium methylate in 250 ml of methanol and the mixture was refluxed for one hour. A solution of 27 g of sodium methylate in 100 ml of methanol were added to the reaction which was cooled to 20° C. and concentrated to dryness. The residue was dissolved in water and the solution was washed with ether, acidified with concentrated hydrochloric acid and was vacuum filtered. The recovered crystals were dried to obtain 42 g of 2-cyano-3-hydroxy-5-methoxy-thiophene with a melting point of 138°-140° C. A microanalytically pure sample obtained by crystallization from isopropyl ether melted at 140° C.
Workup
- temperaturethe mixture was refluxed for one hour
- concentrationconcentrated to dryness
- dissolutionThe residue was dissolved in water
- washthe solution was washed with ether
- filtrationfiltered
- customThe recovered crystals were dried
Sources & evidence
- ORD record
- ord-674dc42c9aa846ea911fcc3cd67a7335
- Source dataset
- uspto-grants-1979_05
- Patent number
- US04155996
Reaction notes
Loading…