No renderable structure data available
COC(=O)CC1CCC(=O)C1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | methyl 2-(3-oxocyclopentyl)acetate |
|---|---|
| IUPAC Name | — |
| CAS Number | 34130-51-3 |
| Database ID | 11355614 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
methyl 2-(3-oxocyclopentyl)acetate (CAS 34130-51-3) 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 11355614
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
11 reactions · 11 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-aa027cd4023740f68159fc0254e339d7Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Tetrahedron, 57 (2001), 5183. A mixture of Montmorillonite K10 (188 g, 571 mmol) in trimethyl orthoformate (316 mL, 2856 mmol) was stirred for 2 hrs under nitrogen. To the mixture was slowly added methyl 2-(3-oxocyclopentyl)acetate (89.2 g, 571 mmol), as a suspension in pentane (500 mL). The mixture was stirred for 16 hrs, then filtered through a CELITE® pad rinsing with pentane. The filtrate was concentrated under reduced pressure to afford the title compound (104.9 g, 519 mmol, 91% yield) as an amber oil. 1H NMR (400 MHz, CDCl3) δ ppm 3.67 (3 H, s) 3.20 (6 H, s) 2.35-2.46 (3 H, m) 2.11 (1 H, dd, J=13.18, 7.40 Hz) 1.86-1.96 (2 H, m) 1.74-1.83 (1 H, m) 1.44 (1 H, dd, J=13.05, 8.53 Hz) 1.34 (1 H, dd, J=12.55, 8.78 Hz). 13C NMR (101 MHz, CDCl3) δ ppm 172.73, 110.91, 50.93, 48.80, 48.61, 40.27, 39.66, 33.51, 33.25, 29.37. The mixture was stirred for 16 hrs filtered through a CELITE® pad rinsing with pentane The filtrate was concentrated under reduced pressure
Source ID: ord-7daed84b522a4d2a8101f39b4feb208fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Tetrahedron, 57 (2001), 5183. A mixture of Montmorillonite K10 (188 g, 571 mmol) in trimethyl orthoformate (316 mL, 2856 mmol) was stirred for 2 hrs under nitrogen. To the mixture was slowly added methyl 2-(3-oxocyclopentyl)acetate (89.2 g, 571 mmol), as a suspension in pentane (500 mL). The mixture was stirred for 16 hrs, then filtered through a CELITE® pad rinsing with pentane. The filtrate was concentrated under reduced pressure to afford the title compound (104.9 g, 519 mmol, 91% yield) as an amber oil. 1H NMR (400 MHz, CDCl3) δ ppm 3.67 (3 H, s) 3.20 (6 H, s) 2.35-2.46 (3 H, m) 2.11 (1 H, dd, J=13.18, 7.40 Hz) 1.86-1.96 (2 H, m) 1.74-1.83 (1 H, m) 1.44 (1 H, dd, J=13.05, 8.53 Hz) 1.34 (1 H, dd, J=12.55, 8.78 Hz). 13C NMR (101 MHz, CDCl3) δ ppm 172.73, 110.91, 50.93, 48.80, 48.61, 40.27, 39.66, 33.51, 33.25, 29.37. The mixture was stirred for 16 hrs filtered through a CELITE® pad rinsing with pentane The filtrate was concentrated under reduced pressure
Source ID: ord-7daed84b522a4d2a8101f39b4feb208fConditions: temp:210.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A 1000 mL flask was charged with dimethyl 2-(3-oxocyclopentyl)malonate (329.1 g, 1536 mmol), and dodecanedioic acid (283 g, 1229 mmol). The mixture was heated (210° C., oil bath) under a nitrogen atmosphere for 20 hrs, then distilled (˜1 torr, 180° C. oil bath) to give the title compound (170.4 g, 1091 mmol, 71.0% yield) as a pale yellow oil. 1H NMR (500 MHz, CDCl3) δ ppm 3.68 (3 H, s), 2.55-2.66 (1 H, m), 2.40-2.51 (3 H, m), 2.27-2.35 (1 H, m), 2.13-2.26 (2 H, m), 1.87 (1 H, ddd, J=18.23, 10.30, 1.37 Hz), 1.53-1.63 (1 H, m). 13C NMR (126 MHz, CDCl3) δ ppm 218.36, 172.58, 51.78, 44.70, 39.53, 38.40, 33.52, 29.31. distilled (˜1 torr, 180° C. oil bath)
Source ID: ord-e07d20f0b0464243a5cc9c09efab9ed3Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-aa027cd4023740f68159fc0254e339d7Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The reductive amination of (S)-2-amino-6-(5-amino-2-fluoro-phenyl)-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one (intermediate J) and (3-oxo-cyclopentyl)-acetic acid methyl ester using decaborane yielded a mixture of isomers of the title compound as a white foam. MS (ESI): m/z=419.3 [M+H]+. yielded
Source ID: ord-a8a2bb4bc5784bb180245fb32ea1f5f2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The reductive amination of (S)-2-amino-6-(5-amino-2-fluoro-phenyl)-3,5,5,6-tetramethyl-5,6-dihydro-3H-pyrimidin-4-one (intermediate J) and (3-oxo-cyclopentyl)-acetic acid methyl ester using decaborane yielded a mixture of isomers of the title compound as a white foam. MS (ESI): m/z=419.3 [M+H]+. yielded
Source ID: ord-a8a2bb4bc5784bb180245fb32ea1f5f2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was prepared following the procedure described in method 2 for the preparation of intermediate 1, Step 6, using methyl 2-(3-oxocyclopentyl)acetate as the reactant. (50.1% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ 5.66 (q, J=2.1 Hz, 1H), 3.73 (br. s., 3H), 3.29-3.13 (m, 1H), 2.95-2.78 (m, 1H), 2.67-2.57 (m, 2H), 2.49-2.40 (m, 1H), 2.40-2.28 (m, 1H), 1.77-1.63 (m, 1H). 19F NMR (376 MHz, CHLOROFORM-d) δ −73.53 (s, 3F).
Source ID: ord-4692fe5a38d44872bfa284624632881bConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Tetrahedron, 57 (2001), 5183. A mixture of Montmorillonite K10 (188 g, 571 mmol) in trimethyl orthoformate (316 mL, 2856 mmol) was stirred for 2 hrs under nitrogen. To the mixture was slowly added methyl 2-(3-oxocyclopentyl)acetate (89.2 g, 571 mmol), as a suspension in pentane (500 mL). The mixture was stirred for 16 hrs, then filtered through a CELITE® pad rinsing with pentane. The filtrate was concentrated under reduced pressure to afford the title compound (104.9 g, 519 mmol, 91% yield) as an amber oil. 1H NMR (400 MHz, CDCl3) δ ppm 3.67 (3 H, s) 3.20 (6 H, s) 2.35-2.46 (3 H, m) 2.11 (1 H, dd, J=13.18, 7.40 Hz) 1.86-1.96 (2 H, m) 1.74-1.83 (1 H, m) 1.44 (1 H, dd, J=13.05, 8.53 Hz) 1.34 (1 H, dd, J=12.55, 8.78 Hz). 13C NMR (101 MHz, CDCl3) δ ppm 172.73, 110.91, 50.93, 48.80, 48.61, 40.27, 39.66, 33.51, 33.25, 29.37. The mixture was stirred for 16 hrs filtered through a CELITE® pad rinsing with pentane The filtrate was concentrated under reduced pressure
Source ID: ord-7daed84b522a4d2a8101f39b4feb208fConditions: temp:210.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A 1000 mL flask was charged with dimethyl 2-(3-oxocyclopentyl)malonate (329.1 g, 1536 mmol), and dodecanedioic acid (283 g, 1229 mmol). The mixture was heated (210° C., oil bath) under a nitrogen atmosphere for 20 hrs, then distilled (˜1 torr, 180° C. oil bath) to give the title compound (170.4 g, 1091 mmol, 71.0% yield) as a pale yellow oil. 1H NMR (500 MHz, CDCl3) δ ppm 3.68 (3 H, s), 2.55-2.66 (1 H, m), 2.40-2.51 (3 H, m), 2.27-2.35 (1 H, m), 2.13-2.26 (2 H, m), 1.87 (1 H, ddd, J=18.23, 10.30, 1.37 Hz), 1.53-1.63 (1 H, m). 13C NMR (126 MHz, CDCl3) δ ppm 218.36, 172.58, 51.78, 44.70, 39.53, 38.40, 33.52, 29.31. distilled (˜1 torr, 180° C. oil bath)
Source ID: ord-e07d20f0b0464243a5cc9c09efab9ed3Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-aa027cd4023740f68159fc0254e339d7PubChem References
These sources are listed in the compound's public database record.
Request a Quote
Send the required specification, quantity, destination and intended use. The CATO team will review availability and respond.