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CCOC(=O)C1=CC=C(N1)CC2=CC=CC=C2Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | ethyl 5-benzyl-1H-pyrrole-2-carboxylate |
|---|---|
| IUPAC Name | — |
| CAS Number | 125261-18-9 |
| Database ID | 14449694 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
ethyl 5-benzyl-1H-pyrrole-2-carboxylate (CAS 125261-18-9) 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 14449694
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-baa4402410ae47e2bf370b5b482a18faConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-4aa27519de314fbb9e9184388c0179c2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of Ethyl 5-benzylpyrrole-2-carboxylate (0.7 g, 3.05 mmol; Elder et al., Synthetic Communications, 19, 763-767 (1989)), ethanol (20 ml) and 1M sodium hydroxide (9.2 ml, 9.2 mmol) was stirred and heated under reflux for 3 h. The major part of the ethanol was removed and the remaining liquid was diluted with water, washed with ether, cooled in ice and acidified with concentrated hydrochloric acid. The mixture was extracted with ether. The combined extracts were washed with brine, dried (Na2SO4) and concentrated to afford 0.567 g (92%) of an off white solid: mp. 130°-134° C.; 1H NMR(CDCl3) δ 8.87 (1H, brs), 7.37-6.95 (5H, m), 6.97 (1H, m), 6.07 (1H, m), 4.00 (2H, s). heated under reflux for 3 h The major part of the ethanol was removed the remaining liquid was diluted with water washed with ether cooled in ice The mixture was extracted with ether The combined extracts were washed with brine dried (Na2SO4) concentrated to afford 0.567 g (92%) of an off white solid
Source ID: ord-91b620575aad4f11aeecefe648793f87Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of Ethyl 5-benzylpyrrole-2-carboxylate (0.7 g, 3.05 mmol; Elder et al., Synthetic Communications, 19, 763-767 (1989)), ethanol (20 ml) and 1M sodium hydroxide (9.2 ml, 9.2 mmol) was stirred and heated under reflux for 3 h. The major part of the ethanol was removed and the remaining liquid was diluted with water, washed with ether, cooled in ice and acidified with concentrated hydrochloric acid. The mixture was extracted with ether. The combined extracts were washed with brine, dried (Na2SO4) and concentrated to afford 0.567 g (92%) of an off white solid: mp. 130°-134° C.; 1H NMR(CDCl3) δ 8.87 (1H, brs), 7.37-6.95 (5H, m), 6.97 (1H, m), 6.07 (1H, m), 4.00 (2H, s). heated under reflux for 3 h The major part of the ethanol was removed the remaining liquid was diluted with water washed with ether cooled in ice The mixture was extracted with ether The combined extracts were washed with brine dried (Na2SO4) concentrated to afford 0.567 g (92%) of an off white solid
Source ID: ord-91b620575aad4f11aeecefe648793f87Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of Ethyl 5-benzylpyrrole-2-carboxylate (0.7 g, 3.05 mmol; Elder et al., Synthetic Communications, 19, 763-767 (1989)), ethanol (20 ml) and 1M sodium hydroxide (9.2 ml, 9.2 mmol) was stirred and heated under reflux for 3 h. The major part of the ethanol was removed and the remaining liquid was diluted with water, washed with ether, cooled in ice and acidified with concentrated hydrochloric acid. The mixture was extracted with ether. The combined extracts were washed with brine, dried (Na2SO4) and concentrated to afford 0.567 g (92%) of an off white solid: mp. 130-134° C.; 1H NMR (CDCl3) δ 8.87 (1H, brs), 7.37-6.95 (5H, m), 6.97 (1H, m), 6.07 (1H, m), 4.00 (2H, s). heated under reflux for 3 h The major part of the ethanol was removed the remaining liquid was diluted with water washed with ether cooled in ice The mixture was extracted with ether The combined extracts were washed with brine dried (Na2SO4) concentrated to afford 0.567 g (92%) of an off white solid
Source ID: ord-f9df90aa38fd4ecd9d8008affd4dc36dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of Ethyl 5-benzylpyrrole-2-carboxylate (0.7 g, 3.05 mmol; Elder et al., Synthetic Communications, 19, 763-767 (1989)), ethanol (20 ml) and 1M sodium hydroxide (9.2 ml, 9.2 mmol) was stirred and heated under reflux for 3 h. The major part of the ethanol was removed and the remaining liquid was diluted with water, washed with ether, cooled in ice and acidified with concentrated hydrochloric acid. The mixture was extracted with ether. The combined extracts were washed with brine, dried (Na2SO4) and concentrated to afford 0.567 g (92%) of an off white solid: mp. 130-134° C.; 1H NMR (CDCl3) δ 8.87 (1H, brs), 7.37-6.95 (5H, m), 6.97 (1H, m), 6.07 (1H, m), 4.00 (2H, s). heated under reflux for 3 h The major part of the ethanol was removed the remaining liquid was diluted with water washed with ether cooled in ice The mixture was extracted with ether The combined extracts were washed with brine dried (Na2SO4) concentrated to afford 0.567 g (92%) of an off white solid
Source ID: ord-f9df90aa38fd4ecd9d8008affd4dc36dConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-baa4402410ae47e2bf370b5b482a18faConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-4aa27519de314fbb9e9184388c0179c2Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of Ethyl 5-benzylpyrrole-2-carboxylate (0.7 g, 3.05 mmol; Elder et al., Synthetic Communications, 19, 763-767 (1989)), ethanol (20 ml) and 1M sodium hydroxide (9.2 ml, 9.2 mmol) was stirred and heated under reflux for 3 h. The major part of the ethanol was removed and the remaining liquid was diluted with water, washed with ether, cooled in ice and acidified with concentrated hydrochloric acid. The mixture was extracted with ether. The combined extracts were washed with brine, dried (Na2SO4) and concentrated to afford 0.567 g (92%) of an off white solid: mp. 130°-134° C.; 1H NMR (CDCl3) δ 8.87 (1H, brs), 7.37-6.95 (5H, m), 6.97 (1H, m), 6.07 (1H, m), 4.00 (2H, s). heated under reflux for 3 h The major part of the ethanol was removed the remaining liquid was diluted with water washed with ether cooled in ice The mixture was extracted with ether The combined extracts were washed with brine dried (Na2SO4) concentrated to afford 0.567 g (92%) of an off white solid
Source ID: ord-b33f7f4973da4dadb0c741e6be8f227dConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of Ethyl 5-benzylpyrrole-2-carboxylate (0.7 g, 3.05 mmol; Elder et al., Synthetic Communications, 19, 763-767 (1989)), ethanol (20 ml) and 1M sodium hydroxide (9.2 ml, 9.2 mmol) was stirred and heated under reflux for 3 h. The major part of the ethanol was removed and the remaining liquid was diluted with water, washed with ether, cooled in ice and acidified with concentrated hydrochloric acid. The mixture was extracted with ether. The combined extracts were washed with brine, dried (Na2SO4) and concentrated to afford 0.567 g (92%) of an off white solid: mp. 130-134° C.; 1H NMR(CDCl3) δ8.87 (1H, brs), 7.37-6.95 (5H, m), 6.97 (1H, m), 6.07 (1H, m), 4.00 (2H, s). heated under reflux for 3 h The major part of the ethanol was removed the remaining liquid was diluted with water washed with ether cooled in ice The mixture was extracted with ether The combined extracts were washed with brine dried (Na2SO4) concentrated to afford 0.567 g (92%) of an off white solid
Source ID: ord-9c0bfda7be6c485482ab6020b1a13d29Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of Ethyl 5-benzylpyrrole-2-carboxylate (0.7 g, 3.05 mmol; Elder et al., Synthetic Communications, 19, 763-767 (1989)), ethanol (20 ml) and 1M sodium hydroxide (9.2 ml, 9.2 mmol) was stirred and heated under reflux for 3 h. The major part of the ethanol was removed and the remaining liquid was diluted with water, washed with ether, cooled in ice and acidified with concentrated hydrochloric acid. The mixture was extracted with ether. The combined extracts were washed with brine, dried (Na2SO4) and concentrated to afford 0.567 g (92%) of an off white solid: mp. 130-134° C.; 1H NMR(CDCl3) δ 8.87 (1H, brs), 7.37-6.95 (5H, m), 6.97 (1H, m), 6.07 (1H, m), 4.00 (2H, s). heated under reflux for 3 h The major part of the ethanol was removed the remaining liquid was diluted with water washed with ether cooled in ice The mixture was extracted with ether The combined extracts were washed with brine dried (Na2SO4) concentrated to afford 0.567 g (92%) of an off white solid
Source ID: ord-ced099db4ebf49238b1fd61f2a866888Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Freshly prepared aq. NaOH (10 M in H2O, 4.78 mmol) was added to a stirring, room temperature solution of 31 (0.2190 g, 0.955 mmol) in MeOH (2.4 mL, 0.4 M) under N2. The reaction was heated to reflux until the reaction was judged complete by HPLC (40 min). The product was concentrated and then dissolved in 1.9 mL H2O. 10% aq. HCl was added dropwise until the pH=2. The white solid that precipitated from the reaction was filtered off and washed with cold H2O. The solid was dried under vacuum overnight to obtain 32 as a pale pink, impure solid (0.0845 g). 32 was further purified by adding CHCl3, stirring, and filtering off pure white 32 (0.0445 g). Note. The undesired impurity has a retention time of 9.643 min by HPLC. Also, the 13C NMR of 32 at room temperature showed doublets for the peaks corresponding to the pyrrole carbons, benzyl carbon, and acid carbon. When the NMR probe was heated to 28° C., all doubled peaks collapsed into single peaks as reported below. 1H (CD3OD, 400 MHz): δ 11.04 (1H, broad s), 7.27-7.13 (5H, m), 6.80 (1H, d, J=3.4 Hz), 5.87 (1H, d, J=3.4 Hz) 3.93 (2H, s) ppm. 13C (CD3OD, 100 MHz): δ 164.52, 140.71, 139.04, 129.56, 129.42, 127.27, 122.77, 117.59, 109.66, 34.65 ppm. DEPT (CD3OD, 100 MHz): CH2 carbons: 34.65; CH carbons: 129.56, 129.42, 127.27, 117.59, 109.66 ppm. HPLC: 8.698 min. The reaction was heated to reflux until the reaction was judged complete by HPLC (40 min) The product was concentrated dissolved in 1.9 mL H2O 10% aq. HCl was added dropwise until the pH=2 The white solid that precipitated from the reaction was filtered off washed with cold H2O The solid was dried under vacuum overnight
Source ID: ord-8ca5e8f026cd449aab17d8d3431e0ca2PubChem References
These sources are listed in the compound's public database record.
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