No renderable structure data available
CCOC(=O)C1(CCCC1)CChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | ethyl 1-methylcyclopentane-1-carboxylate |
|---|---|
| IUPAC Name | — |
| CAS Number | 6553-72-6 |
| Database ID | 12754711 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
ethyl 1-methylcyclopentane-1-carboxylate (CAS 6553-72-6) 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 12754711
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
8 reactions · 8 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-1bf296f9c32c43beb0e5236a166f0da4Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Ethyl 1-methylcyclopentanecarboxylate (47 g, 301 mmol), acetonitrile (14.5 g, 363 mmol), NaH (18 g, 450 mmol), NaOH (6.8 g, 170 mmol) and hydroxylamine hydrochloride (4 g, 57 mmol) were sequentially combined by a procedure analogous to Example B10 to provide 3-(1-methylcyclopentyl)isoxazol-5-amine (7 g, 70% yield over 2 steps). 1H NMR (400 MHz, DMSO-d6): δ 6.41 (s, 2 H), 4.81 (s, 1 H), 1.91-1.86 (m, 2H), 1.67-1.48 (m, 6 H), 1.19 (s, 3 H); MS (ESI) m/z: 167.1 (M+H+).
Source ID: ord-7acd5867d6b84060ab6793e1485ffa06Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Ethyl 1-methylcyclopentanecarboxylate (47 g, 301 mmol), acetonitrile (14.5 g, 363 mmol), NaH (18 g, 450 mmol), NaOH (6.8 g, 170 mmol) and hydroxylamine hydrochloride (4 g, 57 mmol) were sequentially combined by a procedure analogous to Example B10 to provide 3-(1-methylcyclopentyl)isoxazol-5-amine (7 g, 70% yield over 2 steps). 1H NMR (400 MHz, DMSO-d6): δ 6.41 (s, 2 H), 4.81 (s, 1 H), 1.91-1.86 (m, 2H), 1.67-1.48 (m, 6 H), 1.19 (s, 3 H); MS (ESI) m/z: 167.1 (M+H+).
Source ID: ord-7acd5867d6b84060ab6793e1485ffa06Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of nBuLi in hexanes (242 mL, 387 mmol) was added to a −78° C. solution of diisopropylamine (39.1 g, 387 mmol) in anhydrous THF (300 mL) and the resultant mixture was stirred for 30 min at −78° C. A solution of ethyl cyclopentanecarboxylate (50 g, 352 mmol) in anhydrous THF (150 mL) was added dropwise into the mixture and the reaction mixture was stirred at −78° C. for 1 h. Iodomethane (79.2 g, 558 mmol) was added dropwise and the resulting mixture was warmed to RT and stirred overnight. The mixture was poured into water and extracted with ethyl ether. The combined extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give ethyl 1-methylcyclopentanecarboxylate (47 g, 85%). 1H NMR (300 MHz, DMSO-d6): δ 4.03 (q, J=7.2 Hz, 2 H), 1.37-2.03 (m, 8 H), 1.15-1.12 (m, 6 H). the resulting mixture was warmed to RT stirred overnight extracted with ethyl ether The combined extracts were washed with brine dried (MgSO4) concentrated in vacuo
Source ID: ord-910b043089cd4a68b282e22fd1b3c83eConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Ethyl 1-methylcyclopentanecarboxylate (47 g, 301 mmol), acetonitrile (14.5 g, 363 mmol), NaH (18 g, 450 mmol), NaOH (6.8 g, 170 mmol) and hydroxylamine hydrochloride (4 g, 57 mmol) were sequentially combined by a procedure analogous to Example B28 to provide 3-(1-methylcyclopentyl)isoxazol-5-amine (7 g, 70% yield over 2 steps). 1H NMR (400 MHz, DMSO-d6): δ 6.41 (s, 2 H), 4.81 (s, 1 H), 1.91-1.86 (m, 2 H), 1.67-1.48 (m, 6 H), 1.19 (s, 3H); MS (ESI) m/z: 167.1 (M+H+).
Source ID: ord-96ec693ae8fe47e6a775940b5dc889bbConditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of nBuLi in hexanes (242 mL, 387 mmol) was added to a −78° C. solution of thisopropylamine (39.1 g, 387 mmol) in anhydrous THF (300 mL) and the resultant mixture was stirred for 30 min at −78° C. A solution of ethyl cyclopentanecarboxylate (50 g, 352 mmol) in anhydrous THF (150 mL) was added dropwise into the mixture and the reaction mixture was stirred at −78° C. for 1 h. Iodomethane (79.2 g, 558 mmol) was added dropwise and the resulting mixture was warmed to RT and stirred overnight The mixture was poured into water and extracted with ethyl ether. The combined extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give ethyl 1-methylcyclopentanecarboxylate (47 g, 85%). 1H NMR (300 MHz, DMSO-d6): δ 4.03 (q, J=7.2 Hz, 2 H), 1.37-2.03 (m, 8 H), 1.15-1.12 (m, 6H). the resulting mixture was warmed to RT stirred overnight The mixture extracted with ethyl ether The combined extracts were washed with brine dried (MgSO4) concentrated in vacuo
Source ID: ord-5facdc37e6654d1596481ea6a5e444caConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Ethyl 1-methylcyclopentanecarboxylate (47 g, 301 mmol), acetonitrile (14.5 g, 363 mmol), NaH (18 g, 450 mmol), NaOH (6.8 g, 170 mmol) and hydroxylamine hydrochloride (4 g, 57 mmol) were sequentially combined by a procedure analogous to Example B10 to provide 3-(1-methylcyclopentyl)isoxazol-5-amine (7 g, 70% yield over 2 steps). 1H NMR (400 MHz, DMSO-d6): δ 6.41 (s, 2 H), 4.81 (s, 1 H), 1.91-1.86 (m, 2H), 1.67-1.48 (m, 6 H), 1.19 (s, 3 H); MS (ESI) m/z: 167.1 (M+H+).
Source ID: ord-7acd5867d6b84060ab6793e1485ffa06Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of nBuLi in hexanes (242 mL, 387 mmol) was added to a −78° C. solution of diisopropylamine (39.1 g, 387 mmol) in anhydrous THF (300 mL) and the resultant mixture was stirred for 30 min at −78° C. A solution of ethyl cyclopentanecarboxylate (50 g, 352 mmol) in anhydrous THF (150 mL) was added dropwise into the mixture and the reaction mixture was stirred at −78° C. for 1 h. Iodomethane (79.2 g, 558 mmol) was added dropwise and the resulting mixture was warmed to RT and stirred overnight. The mixture was poured into water and extracted with ethyl ether. The combined extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to give ethyl 1-methylcyclopentanecarboxylate (47 g, 85%). 1H NMR (300 MHz, DMSO-d6): δ 4.03 (q, J=7.2 Hz, 2 H), 1.37-2.03 (m, 8 H), 1.15-1.12 (m, 6 H). the resulting mixture was warmed to RT stirred overnight extracted with ethyl ether The combined extracts were washed with brine dried (MgSO4) concentrated in vacuo
Source ID: ord-910b043089cd4a68b282e22fd1b3c83ePubChem References
These sources are listed in the compound's public database record.
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