Thiophene → HCID 178511484, compound
Reaction equation
C12C3C1C23.[S:5]1[CH:9]=[CH:8][CH:7]=[CH:6]1.C([Li:14])CCC.[Cu:15][C:16]#[N:17]>O1CCCC1>[S:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[Cu-:15][C:16]#[N:17].[Li+:14]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -25 °C
Procedure
Lithium thienyl copper(I) cyanide was prepared according to the method of B. Lipshutz, et al., Tetrahedran Letters, 1987, 28, 945. To a cooled (-30° C.) tetrahydrofuran (100 mL) solution of thiophene (freshly distilled, 15.96 g, 15.2 mL, 0.19 mole) was added n-butyllithium (2.4 M in hexane, 79.2 mL, 0.19 mole) dropwise, via syringe, at a rate such that the temperature did not exceed -17° C. The homogenous mixture was was stirred at -25° C. for 5 min, warmed to 0° C. for 30 min and then recooled to -25° C. This solution was then added via cannula to a vigorously stirred suspension of copper(I) cyanide (16.91 g, 0.19 mole) in cooled (-25° C.) tetrahydrofuran (120 mL) at such a rate that the temperature did not exceed -20° C. The initial hsterogenous mixture was stirred at .25° C. for 1.5 h during which time all the solids dissolved resulting in a deep amber colored homogeneous solution of lithium thienyl copper(I) cyanide.
Workup
- customLithium thienyl copper(I) cyanide was prepared
- distillationfreshly distilled
- customvia syringe, at a rate such that the temperature did not exceed -17° C
- temperaturewarmed to 0° C. for 30 min
- customrecooled to -25° C
- customdid not exceed -20° C
- stirringThe initial hsterogenous mixture was stirred at .25° C. for 1.5 h during which time all the solids
- dissolutiondissolved
Sources & evidence
- ORD record
- ord-1acf15de86274cbe901372c59fb5dc4b
- Source dataset
- uspto-grants-1990_08
- Patent number
- US04952710
Reaction notes
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