Copper and secondary amine‐catalyzed pyridine synthesis from o‐acetyl oximes and α,β-unsaturated aldehydes
A. Acetophenone O-acetyl oxime (1). A 250-mL, two-necked roundbottomed flask equipped with a Teflon-coated magnetic stir bar (oval, 20 x 10 mm) is charged with acetophenone (9.33 mL, 80.0 mmol, 1 equiv) (Note 2), pyridine (18 mL, 223 mmol, 2.8 equiv) (Note 3), ethanol (40 mL) (Note 4), and hydroxyl...
| Main Authors: | , , , |
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| Format: | Journal Article |
| Language: | English |
| Published: |
2020
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| Online Access: | https://hdl.handle.net/10356/139034 |
| _version_ | 1811683373972717568 |
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| author | Tan, Wei Wen Wu, Bin Wei, Ye Yoshikai, Naohiko |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Tan, Wei Wen Wu, Bin Wei, Ye Yoshikai, Naohiko |
| author_sort | Tan, Wei Wen |
| collection | NTU |
| description | A. Acetophenone O-acetyl oxime (1). A 250-mL, two-necked roundbottomed flask equipped with a Teflon-coated magnetic stir bar (oval, 20 x 10 mm) is charged with acetophenone (9.33 mL, 80.0 mmol, 1 equiv)
(Note 2), pyridine (18 mL, 223 mmol, 2.8 equiv) (Note 3), ethanol (40 mL) (Note 4), and hydroxylamine hydrochloride (8.33 g, 120 mmol, 1.5 equiv) (Note 5). The resulting mixture is stirred at 60 °C for 75 min (Notes 6 and 7) (Figure 1) and then cooled to 22 °C. Water (80 mL) is added, and the resulting biphasic mixture is transferred to a 500-mL separatory funnel. |
| first_indexed | 2024-10-01T04:11:43Z |
| format | Journal Article |
| id | ntu-10356/139034 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:11:43Z |
| publishDate | 2020 |
| record_format | dspace |
| spelling | ntu-10356/1390342023-02-28T20:00:56Z Copper and secondary amine‐catalyzed pyridine synthesis from o‐acetyl oximes and α,β-unsaturated aldehydes Tan, Wei Wen Wu, Bin Wei, Ye Yoshikai, Naohiko School of Physical and Mathematical Sciences Science::Chemistry Acetophenone Hydroxylamine Hydrochloride A. Acetophenone O-acetyl oxime (1). A 250-mL, two-necked roundbottomed flask equipped with a Teflon-coated magnetic stir bar (oval, 20 x 10 mm) is charged with acetophenone (9.33 mL, 80.0 mmol, 1 equiv) (Note 2), pyridine (18 mL, 223 mmol, 2.8 equiv) (Note 3), ethanol (40 mL) (Note 4), and hydroxylamine hydrochloride (8.33 g, 120 mmol, 1.5 equiv) (Note 5). The resulting mixture is stirred at 60 °C for 75 min (Notes 6 and 7) (Figure 1) and then cooled to 22 °C. Water (80 mL) is added, and the resulting biphasic mixture is transferred to a 500-mL separatory funnel. Accepted version 2020-05-15T02:08:02Z 2020-05-15T02:08:02Z 2019 Journal Article Tan, W. W., Wu, B., Wei, Y., & Yoshikai, N. (2018). Copper and secondary amine‐catalyzed pyridine synthesis from o‐acetyl oximes and α,β-unsaturated aldehydes. Organic Syntheses, 95, 1-14. doi:10.1002/0471264229.os095.01 9780471264224 0078-6209 https://hdl.handle.net/10356/139034 10.1002/0471264229.os095.01 2-s2.0-85072078793 95 1 14 en Organic Syntheses © 2018 Organic Syntheses. All rights reserved. This paper was published in Organic Syntheses and is made available with permission of Organic Syntheses. application/pdf |
| spellingShingle | Science::Chemistry Acetophenone Hydroxylamine Hydrochloride Tan, Wei Wen Wu, Bin Wei, Ye Yoshikai, Naohiko Copper and secondary amine‐catalyzed pyridine synthesis from o‐acetyl oximes and α,β-unsaturated aldehydes |
| title | Copper and secondary amine‐catalyzed pyridine synthesis from o‐acetyl oximes and α,β-unsaturated aldehydes |
| title_full | Copper and secondary amine‐catalyzed pyridine synthesis from o‐acetyl oximes and α,β-unsaturated aldehydes |
| title_fullStr | Copper and secondary amine‐catalyzed pyridine synthesis from o‐acetyl oximes and α,β-unsaturated aldehydes |
| title_full_unstemmed | Copper and secondary amine‐catalyzed pyridine synthesis from o‐acetyl oximes and α,β-unsaturated aldehydes |
| title_short | Copper and secondary amine‐catalyzed pyridine synthesis from o‐acetyl oximes and α,β-unsaturated aldehydes |
| title_sort | copper and secondary amine catalyzed pyridine synthesis from o acetyl oximes and α β unsaturated aldehydes |
| topic | Science::Chemistry Acetophenone Hydroxylamine Hydrochloride |
| url | https://hdl.handle.net/10356/139034 |
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