Synthesis of polyfunctionalized 1,3-diols through a one-pot "double nitroaldol reaction-ring cleavage" of 2-nitrocycloalkanones

Synlett

Volumn , Issue 12, 1997, Pages 1389-1390

  Ballini, Roberto ^a   Barboni, Luciano ^a   Pintucci, Lorenzo ^a  

^a Dipartimento di Scienze Chimiche   (Italy)

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EID: 0345412261     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (36)

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22. A representative procedure is as follows: Prepartion of 2-nitro-1,3-diols 2:To a solution of potassium carbonate (276 mg, 2 mmol) in 5 ml of water, formaldehyde (0.233 ml of 30% water solution, 3 mmol) and 2-nitrocycloalkanone (1 mmol) were added. After stirring overnight at room temperature (50°C for the preparation of 2i) 10 ml of water was added, the solution was acidified with 10% hydrochloric acid and extracted with EtOAc (5 × 10 ml). The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure to leave a crude product which was purified by reversed-phase chromatography (sometimes yields decreased owing to partial decomposition of nitrodiols on LiChroprep).
23. 1H NMR (DMSO): δ = 1.18 (2H, m), 1.46 (2H, m), 1.78 (2H, m), 2.18 (2H, t, J = 8.5 Hz), 3.70 (4H, dd, J = 15.3 and 11.9 Hz).
24. 6: C, 56.77; H, 8.57; N, 4.41. Found: C, 56.55; H, 8.66; N, 4.31.
25. 4: C, 60.68; H, 9.01; N, 5.44. Found: C, 60.83; H, 8.96; N, 5.36.
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