No renderable structure data available
CCC1CC(=O)C=CN1C(=O)OCC2=CC=CC=C2Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | benzyl 2-ethyl-4-oxo-2,3-dihydropyridine-1-carboxylate |
|---|---|
| IUPAC Name | — |
| CAS Number | 919366-32-8 |
| Database ID | 53419195 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
benzyl 2-ethyl-4-oxo-2,3-dihydropyridine-1-carboxylate (CAS 919366-32-8) 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 53419195
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
9 reactions · 9 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-4fdb96770a5e428282782c69b426c046Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: CuBr.SMe2 (5.6 g, 27.2 mmol) was added to dry THF (64 mL). It was cooled to −78° C. 4-Chlorophenylmagnesium bromide (27.2 mL, 1 M in THF, 27.2 mmol) was added to the mixture slowly over 1 hr at −78° C. Then BF3.Et2O (3.44 mL, 27.2 mmol) was added and the mixture was stirred for 5 min. Then ketone 82 (4 g, 8.1 mmol) in THF (55 mL) was added slowly over 1 hr at −78° C. After 2 hr stirring at −78° C., an aqueous solution of NH4Cl/conc. NH4OH (1:1, 20%, 60 mL) was added. The mixture was warmed to rt and extracted with EtOAc (200 mL×3), The combined organic layers were washed with brine, dried and concentrated to a residue and purified by silica gel chromatography (0-40% EtOAc/hexanes) to afford pure 83 (1 g, 2.7 mmol, 33%) as a mixture of cis stereoisomers. After 2 hr stirring at −78° C. The mixture was warmed to rt extracted with EtOAc (200 mL×3) The combined organic layers were washed with brine dried concentrated to a residue purified by silica gel chromatography (0-40% EtOAc/hexanes)
Source ID: ord-7b77112cbcbd41cea3bf4f3c5c428bdaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-methoxylpyridine 81 (4.41 g, 40.5 mmol) in toluene (200 mL) at −20° C. was added CbzCl (5.7 ml, 40.5 mmol) in toluene (200 mL) dropwise. After 15 min, ethylmagnesium bromide (23 mL, 2M in THF, 46 mmol) was added dropwise. After 1 hr, 10% aqueous HCl (100 mL) was added and the mixture stirred overnight. The mixture was separated and the organic layer was washed with sat. NaHCO3 and brine. It was dried and concentrated to afford 82 (9 g, 36.4 mmol, 89.9%) that was used directly in the next reaction. After 1 hr The mixture was separated the organic layer was washed with sat. NaHCO3 and brine It was dried concentrated
Source ID: ord-5516529a5feb4309858df49e05ee3eccConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-4fdb96770a5e428282782c69b426c046Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: CuBr.SMe2 (5.6 g, 27.2 mmol) was added to dry THF (64 mL). It was cooled to −78° C. 4-Chlorophenylmagnesium bromide (27.2 mL, 1 M in THF, 27.2 mmol) was added to the mixture slowly over 1 hr at −78° C. Then BF3.Et2O (3.44 mL, 27.2 mmol) was added and the mixture was stirred for 5 min. Then ketone 82 (4 g, 8.1 mmol) in THF (55 mL) was added slowly over 1 hr at −78° C. After 2 hr stirring at −78° C., an aqueous solution of NH4Cl/conc. NH4OH (1:1, 20%, 60 mL) was added. The mixture was warmed to rt and extracted with EtOAc (200 mL×3), The combined organic layers were washed with brine, dried and concentrated to a residue and purified by silica gel chromatography (0-40% EtOAc/hexanes) to afford pure 83 (1 g, 2.7 mmol, 33%) as a mixture of cis stereoisomers. After 2 hr stirring at −78° C. The mixture was warmed to rt extracted with EtOAc (200 mL×3) The combined organic layers were washed with brine dried concentrated to a residue purified by silica gel chromatography (0-40% EtOAc/hexanes)
Source ID: ord-7b77112cbcbd41cea3bf4f3c5c428bdaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-methoxylpyridine 81 (4.41 g, 40.5 mmol) in toluene (200 mL) at −20° C. was added CbzCl (5.7 ml, 40.5 mmol) in toluene (200 mL) dropwise. After 15 min, ethylmagnesium bromide (23 mL, 2M in THF, 46 mmol) was added dropwise. After 1 hr, 10% aqueous HCl (100 mL) was added and the mixture stirred overnight. The mixture was separated and the organic layer was washed with sat. NaHCO3 and brine. It was dried and concentrated to afford 82 (9 g, 36.4 mmol, 89.9%) that was used directly in the next reaction. After 1 hr The mixture was separated the organic layer was washed with sat. NaHCO3 and brine It was dried concentrated
Source ID: ord-5516529a5feb4309858df49e05ee3eccConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-4fdb96770a5e428282782c69b426c046Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: CuBr.SMe2 (5.6 g, 27.2 mmol) was added to dry THF (64 mL). It was cooled to −78° C. 4-Chlorophenylmagnesium bromide (27.2 mL, 1 M in THF, 27.2 mmol) was added to the mixture slowly over 1 hr at −78° C. Then BF3.Et2O (3.44 mL, 27.2 mmol) was added and the mixture was stirred for 5 min. Then ketone 82 (4 g, 8.1 mmol) in THF (55 mL) was added slowly over 1 hr at −78° C. After 2 hr stirring at −78° C., an aqueous solution of NH4Cl/conc. NH4OH (1:1, 20%, 60 mL) was added. The mixture was warmed to rt and extracted with EtOAc (200 mL×3), The combined organic layers were washed with brine, dried and concentrated to a residue and purified by silica gel chromatography (0-40% EtOAc/hexanes) to afford pure 83 (1 g, 2.7 mmol, 33%) as a mixture of cis stereoisomers. After 2 hr stirring at −78° C. The mixture was warmed to rt extracted with EtOAc (200 mL×3) The combined organic layers were washed with brine dried concentrated to a residue purified by silica gel chromatography (0-40% EtOAc/hexanes)
Source ID: ord-7b77112cbcbd41cea3bf4f3c5c428bdaConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 4-methoxylpyridine 81 (4.41 g, 40.5 mmol) in toluene (200 mL) at −20° C. was added CbzCl (5.7 ml, 40.5 mmol) in toluene (200 mL) dropwise. After 15 min, ethylmagnesium bromide (23 mL, 2M in THF, 46 mmol) was added dropwise. After 1 hr, 10% aqueous HCl (100 mL) was added and the mixture stirred overnight. The mixture was separated and the organic layer was washed with sat. NaHCO3 and brine. It was dried and concentrated to afford 82 (9 g, 36.4 mmol, 89.9%) that was used directly in the next reaction. After 1 hr The mixture was separated the organic layer was washed with sat. NaHCO3 and brine It was dried concentrated
Source ID: ord-5516529a5feb4309858df49e05ee3eccPubChem References
These sources are listed in the compound's public database record.
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