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Chemistry
Heterocyclic Building Blocks
Benzofurans
(5-Nitrobenzofuran-2-yl)methanol
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Heterocyclic Building Blocks
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[ CAS No. 90322-48-8 ] {[proInfo.proName]}

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Chemical Structure| 90322-48-8
Chemical Structure| 90322-48-8
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CAS No. :90322-48-8 MDL No. :MFCD10758066
Formula : C9H7NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 193.16 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 90322-48-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 90322-48-8 ]

[ 90322-48-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 89487-91-2 ]
  • [ 107-19-7 ]
  • [ 90322-48-8 ]
Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 8221 - 8225
  • 2
  • [ 10242-12-3 ]
  • [ 541-41-3 ]
  • [ 90322-48-8 ]
YieldReaction ConditionsOperation in experiment
91.2% With 4-methyl-morpholine; hydrogenchloride; sodium borohydrid; In tetrahydrofuran; N,N-dimethyl-formamide; (1) <strong>[10242-12-3]5-Nitro-1-benzofuran-2-carboxylic acid</strong> (4.0 g, 19.31 mmol) was dissolved in tetrahydrofuran (40 ml), and N-methylmorpholine (2.55 ml, 23.17 mmol) was added. Ethyl chlorocarbonate (2.22 ml, 23.17 mmol) was added dropwise under ice-cooling, and the mixture was stirred for 30 minutes. A solution of sodium borohydride (2.19 g, 57.93 mmol) in N,N-dimethylformamide (40 ml) was added dropwise at -40 C., and the mixture was stirred at the same temperature for 2 hours. 1N hydrochloric acid was added, followed by extraction with ethyl acetate. The organic layer was washed with water and an aqueous saturated sodium chloride solution. The organic layer was dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1), and dried under reduced pressure (50 C.) to obtain (5-nitro-1-benzofuran-2-yl)methanol (3.4 g, yield 91.2%) as a pale yellow crystal. m.p. 115.3-116.3 C. 1H-NMR (200 MHz, CDCl3) delta: 2.04 (1H, t, J=6.2 Hz), 4.84 (2H, d, J=6.2 Hz), 6.83 (1H, s), 7.55 (1H, d, J=9.0 Hz), 8.23 (1H, dd, J=9.0, 2.2 Hz), 8.50 (1H, d, J=2.2 Hz). IR (KBr) 3517, 3108, 1507, 1352 cm-1. Elemental Analysis (C9H7NO4) Cal'd: C, 55.96; H, 3.65; N, 7.25. Found: C, 55.72; H, 3.49; N, 7.35.
Reference： [1]Patent: US2003/78251,2003,A1
  • 3
  • [ 69604-00-8 ]
  • [ 90322-48-8 ]
YieldReaction ConditionsOperation in experiment
87% With lithium borohydride; In methanol; at 20℃; for 4h; Specifically, a mixture of 23 (4.0 g, 17.0 mmol), MeOH (0.82 g, 25.5 mmol) and lithium borohydride (0.56 g, 25.5 mmol) in ether (80 ml_) was stirred at ambient temperature for 4 h. The mixture was diluted with ethyl acetate and washed with 1 N HCI and brine, dried (MgSO4),, and concentrated to afford 24 (3.08 g, 87%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) delta 8.59 (d, J = 2.4 Hz, 1H), 8.19 (dd, J = 9.0, 2.5 Hz, 1 H), 7.80 (d, J = 9.0 Hz, 1 H), 7.00 (s, 1 H), 5.65 (t, J = 5.9 Hz, 1 H), 4.63 (d, J = 5.6 Hz, 2H).
63.5% With methanol; sodium tetrahydroborate; In tetrahydrofuran; for 1h;Cooling with ice; <strong>[69604-00-8]5-nitrobenzofuran-2-carboxylic acid ethyl ester</strong>(10 mmol, 2.35 g) was dissolved in a solution of tetrahydrofuran and methanol (60 ml: 5 ml), and sodium borohydride powder (30 mmol, 1.2 g) was added thereto under an ice bath condition, and the reaction was continued under the ice bath for 1 h. After the reaction was resumed at room temperature, the reaction solution was spotted to determine the end point. Then the solution was poured into cold water (200ml) to terminate the reaction. The pH of the solution was adjusted to 7. The THF and CH3OH were removed by rotary evaporation. The ester (4: 1) was passed through the column to give the product 2d (1.23 g, 63.5%).
2.27 g of NaBH4 are added, in small portions over a period of 8 hours, to 1.12 g of <strong>[69604-00-8]ethyl 5-nitrobenzo[b]furan-2-carboxylate</strong> in 50 ml of THF, and the mixture is then stirred for 40 hours. 5 ml of methanol and then 5 ml of water are added. The reaction medium is extracted with EtOAc, and the organic phase is washed with water, with a 5% KHSO4/K2SO4 solution, with water, and then with a saturated NaCl solution. After drying and concentration under reduced pressure, 0.74 g of the expected product are recovered in solid form.
Reference： [1]Patent: WO2007/30680,2007,A2 .Location in patent: Page/Page column 167-168
[2]Patent: CN110437281,2019,A .Location in patent: Paragraph 0047-0049
[3]Patent: US2008/176874,2008,A1 .Location in patent: Page/Page column 5

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