Reaction #4170503
Related Literature (1)
openreactiondata ↗doi:10.1039/C8SC04228D
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-1b13f95ac94346a7995b14d5b169e038No renderable structure data available
C1CC2=CC=CC=C2C1C#NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2,3-dihydro-1H-indene-1-carbonitrile |
|---|---|
| IUPAC Name | — |
| CAS Number | 26452-97-1 |
| Database ID | 3015277 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2,3-dihydro-1H-indene-1-carbonitrile (CAS 26452-97-1) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 3015277
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-1b13f95ac94346a7995b14d5b169e038Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-1b13f95ac94346a7995b14d5b169e038Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2(2-bromoethyl)-1,3-dioxolane (14.09 ml, 120.1 mmole) was added to a solution of 1-indanecarbonitrile (15.63 g, 109.2 mmole) in 100 ml of THF and cooled to 0° C. After the dropwise addition of 1M LHMDS (120 ml) the solution was stirred at 0° C. for 20 min then at room temperature for 20 min. After the removal of solvent the residue was flashed of silica using 15% EtOAc and Hexanes to afford 1-[2-(1,3-dioxolan-2-yl)ethyl]-1-indanecarbonitrile as a thick oil. at room temperature for 20 min After the removal of solvent the residue
Source ID: ord-79a6e637825f4880bd9a1b42af2b2b27Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2(2-bromoethyl)-1,3-dioxolane (14.09 ml, 120.1 mmole) was added to a solution of 1-indanecarbonitrile (15.63 g, 109.2 mmole) in 100 ml of THF and cooled to 0° C. After the dropwise addition of 1M LHMDS (120 ml) the solution was stirred at 0° C. for 20 min then at room temperature for 20 min. After the removal of solvent the residue was flashed of silica using 15% EtOAc and Hexanes to afford 1-[2-(1,3-dioxolan-2-yl)ethyl]-1-indanecarbonitrile as a thick oil. at room temperature for 20 min After the removal of solvent the residue
Source ID: ord-79a6e637825f4880bd9a1b42af2b2b27Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-bromomethyl-1,3-dioxolane (12.94 ml, 125.0 mmole) was added to a solution of 1-indanecarbonitrile (16.27 g, 113.6 mmole) in 100 ml of THF and cooled to 0° C. After the dropwise addition of 1M LHMDS (125 ml) the solution was stirred at 0° C. for 20 min then at room temperature for 20 min. After the removal of solvent the residue was flashed of silica using 15% EtOAc and Hexanes to afford 19.23 g of 1-(1,3-dioxolan-2-ylmethyl)-1-indanecarbonitrile (74% yield) as a thick oil. at room temperature for 20 min After the removal of solvent the residue
Source ID: ord-46657b17b78c4458a39adbecd34ffc07Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A suspension of 5% Pd on carbon in a solution of 1H-indene-3-carbonitrile in EtOH (200 ml) was placed under an atmosphere of hydrogen with vigorous stirring overnight. After removal of excess hydrogen from the reaction the solution as filtered through celite and concentrated to an oil. The resulting oil was re-dissolved in EtOH and filtered a second time to remove the remaining carbon and catalyst. Evaporation of solvent afforded 12.0108 g of 1-indanecarbonitrile (95% yield) as an oil. After removal of excess hydrogen from the reaction the solution as filtered through celite concentrated to an oil The resulting oil was re-dissolved in EtOH filtered a second time to remove the remaining carbon and catalyst Evaporation of solvent
Source ID: ord-23420e92f45648c39a3d083c53ea4321Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2(2-bromoethyl)-1,3-dioxolane (14.09 ml, 120.1 mmole) was added to a solution of 1-indanecarbonitrile (15.63 g, 109.2 mmole) in 100 ml of THF and cooled to 0° C. After the dropwise addition of 1M LHMDS (120 ml) the solution was stirred at 0° C. for 20 min then at room temperature for 20 min. After the removal of solvent the residue was flashed of silica using 15% EtOAc and Hexanes to afford 1-[2-(1,3-dioxolan-2-yl)ethyl]-1-indanecarbonitrile as a thick oil. at room temperature for 20 min After the removal of solvent the residue
Source ID: ord-0c00347359e8478695a1af3217bb49b6Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2(2-bromoethyl)-1,3-dioxolane (14.09 ml, 120.1 mmole) was added to a solution of 1-indanecarbonitrile (15.63 g, 109.2 mmole) in 100 ml of THF and cooled to 0° C. After the dropwise addition of 1M LHMDS (120 ml) the solution was stirred at 0° C. for 20 min then at room temperature for 20 min. After the removal of solvent the residue was flashed of silica using 15% EtOAc and Hexanes to afford 1-[2-(1,3-dioxolan-2-yl)ethyl]-1-indanecarbonitrile as a thick oil. at room temperature for 20 min After the removal of solvent the residue
Source ID: ord-0c00347359e8478695a1af3217bb49b6Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2-bromomethyl-1,3-dioxolane (12.94 ml, 125.0 mmole) was added to a solution of 1-indanecarbonitrile (16.27 g, 113.6 mmole) in 100 ml of THF and cooled to 0° C. After the dropwise addition of 1M LHMDS (125 ml) the solution was stirred at 0° C. for 20 min then at room temperature for 20 min. After the removal of solvent the residue was flashed of silica using 15% EtOAc and Hexanes to afford 19.23 g of 1-(1,3-dioxolan-2-ylmethyl)-1-indanecarbonitrile (74% yield) as a thick oil. at room temperature for 20 min After the removal of solvent the residue
Source ID: ord-42a352fc69294c78b8d1a546c2bb1f96Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A suspension of 5% Pd on carbon in a solution of 1H-indene-3-carbonitrile in EtOH (200 ml) was placed under an atmosphere of hydrogen with vigorous stirring overnight. After removal of excess hydrogen from the reaction the solution as filtered through celite and concentrated to an oil. The resulting oil was re-dissolved in EtOH and filtered a second time to remove the remaining carbon and catalyst. Evaporation of solvent afforded 12.0108 g of 1-indanecarbonitrile (95% yield) as an oil. After removal of excess hydrogen from the reaction the solution as filtered through celite concentrated to an oil The resulting oil was re-dissolved in EtOH filtered a second time to remove the remaining carbon and catalyst Evaporation of solvent
Source ID: ord-bd747d5eb86c4fe3aa95844850269230Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A suspension of 5% Pd on carbon in a solution of 1H-indene-3-carbonitrile in EtOH (200 ml) was placed under an atmosphere of hydrogen with vigorous stirring overnight. After removal of excess hydrogen from the reaction the solution as filtered through celite and concentrated to an oil. The resulting oil was re-dissolved in EtOH and filtered a second time to remove the remaining carbon and catalyst. Evaporation of solvent afforded 12.0108 g of 1-indanecarbonitrile (95% yield) as an oil. After removal of excess hydrogen from the reaction the solution as filtered through celite concentrated to an oil The resulting oil was re-dissolved in EtOH filtered a second time to remove the remaining carbon and catalyst Evaporation of solvent
Source ID: ord-bd747d5eb86c4fe3aa95844850269230Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 2(2-bromoethyl)-1,3-dioxolane (14.09 ml, 120.1 mmole) was added to a solution of 1-indanecarbonitrile (15.63 g, 109.2 mmole) in 100 ml of THF and cooled to 0° C. After the dropwise addition of 1M LHMDS (120 ml) the solution was stirred at 0° C. for 20 min then at room temperature for 20 min. After the removal of solvent the residue was flashed of silica using 15% EtOAc and Hexanes to afford 1-[2-(1,3-dioxolan-2-yl)ethyl]-1-indanecarbonitrile as a thick oil. at room temperature for 20 min After the removal of solvent the residue
Source ID: ord-79a6e637825f4880bd9a1b42af2b2b27PubChem References
These sources are listed in the compound's public database record.
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