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[ CAS No. 196799-45-8 ]

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Chemical Structure| 196799-45-8
Chemical Structure| 196799-45-8
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CAS No. :196799-45-8 MDL No. :MFCD06200853
Formula : C9H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :148.16 g/mol Pubchem ID :2795018
Synonyms :

Safety of [ 196799-45-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 196799-45-8 ]

  • Upstream synthesis route of [ 196799-45-8 ]
  • Downstream synthetic route of [ 196799-45-8 ]

[ 196799-45-8 ] Synthesis Path-Upstream   1~13

  • 1
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  • [ 4885-02-3 ]
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Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 3, p. 322 - 330
[2] Patent: US2005/187282, 2005, A1, . Location in patent: Page/Page column 8
  • 2
  • [ 68-12-2 ]
  • [ 281678-66-8 ]
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YieldReaction ConditionsOperation in experiment
100%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 0.25 h;
Stage #2: at -40℃; for 1.5 h;
A solution of n-butyl lithium (1.54M-n-hexane solution, 29.2ml, 44.97mmol) in THF (40ml) was added with a solution of Step 1 compound (4.75g, 15.00mmol) in THF (20ml) at -40°C and stirred for 15 minutes. Next, DMF (2.19g, 44.97mmol) was added and the mixture was stirred at -40°C for 1.5 hours. The reaction was stopped by adding water, and the reaction solution was concentrated. Liquid separation was carried out with ethyl acetate-water, the organic layer was washed with 1M-hydrochloric acid and saturated sodium chloride water, dried with anhydrous sodium sulfate, and concentrated to obtain the title compound (2.32g, quant) as a colorless crystal. 1H-NMR (300MHz, CDCl3) δ=3.25 (2H, t, J=7.2Hz), 4.74 (2H, t, J=7.2Hz), 6.93 (1H, t, J=7.5Hz), 7.41 (2H, d, J=7.5Hz), 7.58 (1H, d, J=7.5Hz), 10.20 (1H, s).
Reference: [1] Patent: EP1878734, 2008, A1, . Location in patent: Page/Page column 15
[2] Advanced Synthesis and Catalysis, 2007, vol. 349, # 1-2, p. 193 - 203
[3] Tetrahedron Letters, 2000, vol. 41, # 14, p. 2269 - 2273
  • 3
  • [ 151155-53-2 ]
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YieldReaction ConditionsOperation in experiment
77% With manganese(IV) oxide In toluene at 60℃; for 3 h; A mixture of (2,3-dihydrobenzofuran-7-yl)methanol (9.76 g, 64.99 mmol) and manganese dioxide (45.2 g, 519.93 mmol) in toluene (250 mL) was stirred at 60°C for 3 hr. The manganese dioxide was filtered off, and the filtrate was concentrated under reduced pressure. The precipitate was collected by filtration and washed with cooled hexane to give 2,3-dihydrobenzofuran-7-carbaldehyde (7.43 g, 50.1 mmol, 77percent) as a pale yellow solid.
Reference: [1] Patent: TW2016/2105, 2016, A, . Location in patent: Paragraph 1203
[2] Patent: WO2007/25307, 2007, A2, . Location in patent: Page/Page column 305 - 306
[3] Patent: WO2008/106139, 2008, A1, . Location in patent: Page/Page column 475
  • 4
  • [ 1037763-65-7 ]
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YieldReaction ConditionsOperation in experiment
54% With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1.25 h; A suspension of lithium aluminum hydride (pellets, 5,56 g, 146.5 mmol) in 500 mL of dry THF was allowed to stir at 55 CC for 18 hours under anhydrous atmosphere, then cooled to 0 0C. and a solution of compound 2A (23.37 g. 1 ] 2.7 mmol) in 500 mL of dry THF was added <n="57"/>over 45 minutes. The reaction mixture was allowed to stir at 0 0C for 30 minutes, then quenched by careful addition of aqueous 20percent sodium hydrogen sulfate until gas evolution stopped. Additional aqueous 20percent sodium hydrogen sulfate (approx. 5 mL) was added, and the resulting solution was vigorously allowed to stirfor 15 minutes. The reaction mixture wsa diluted with ether (500 mL) and hexanes (500 mL) and filtered through a short path of celite. The filtrate was concentrated in vacuo to provide a crude residue which was purified using medium pressure liquid chromatography (Biotage 75-M silica gel column, gradient: 0 to 30 percent ethyl acetate in hexanes) to provide compound IB (9.00 g, 54 percent) as a white solid. 1H NMR (400 MHz, d6-DMSO): δlψ.10 (s, IH), 7.51 (q, J= 7.32 Hz 5.13 Hz, 2H), 6.95 (t, J= 7.69 Hz, IH), 4.69 (t, J- 8.79 Hz, 2H), 3.22 (t, J= 8.42 Hz, 2H).
54%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1.25 h;
Stage #2: With sodium hydrogen sulfate; water In tetrahydrofuran
Step B - Synthesis of Compound 59B; A suspension of lithium aluminum hydride (pellets, 5.56 g, 146.5 mmol) in 500 mL of dry THF was allowed to stir at 55 °C for 18 hours under anhydrous atmosphere, then cooled to 0 0C, and a solution of compound 59A (23.37 g, 112.7 mmol) in 500 mL of dry THF was added over 45 minutes. The reaction mixture was allowed to stir at 0 °C for 30 minutes, then quenched by careful addition of aqueous 20percent sodium hydrogen sulfate until gas evolution stopped. Additional aqueous 20percent sodium hydrogen sulfate (approx. 5 mL) was added, and the resulting solution was vigorously allowed to stirfor 15 minutes. The reaction mixture wsa diluted with ether (500 mL) and hexanes (500 mL) and filtered through a short path of celite. The filtrate was concentrated in vacuo to afford a crude residue which was purified using medium pressure liquid chromatography (Biotage 75-M silica gel column, gradient: 0 to 30 percent ethyl acetate in hexanes) to provide compound 59B (9.00 g, 54 percent) as a white solid. 1H NMR (400 MHz, (I6-DMSO): δlψ.10 (s, IH), 7.51 (q, J= 7.32 Hz 5.13 Hz, 2H), 6.95 (t, J= 7.69 Hz, IH), 4.69 (t, J= 8.79 Hz, 2H), 3.22 (t, J= 8.42 Hz, 2H).
Reference: [1] Patent: WO2009/152200, 2009, A1, . Location in patent: Page/Page column 54; 55
[2] Patent: WO2008/82484, 2008, A1, . Location in patent: Page/Page column 163-164
[3] Organic Letters, 2012, vol. 14, # 2, p. 556 - 559
  • 5
  • [ 496-16-2 ]
  • [ 4885-02-3 ]
  • [ 55745-70-5 ]
  • [ 196799-45-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 3, p. 322 - 330
[2] Patent: US2005/187282, 2005, A1, . Location in patent: Page/Page column 8
  • 6
  • [ 496-16-2 ]
  • [ 20485-44-3 ]
  • [ 196799-45-8 ]
YieldReaction ConditionsOperation in experiment
35% With n-butyllithium In <i>N</i>-methyl-acetamide; hexane; water; ethyl acetate; Petroleum ether (1)
7-Formyl-2,3-dihydrobenzofuran
108 ml of an n-butyllithium solution (2.1M) in hexane and 26.7 g (230 mmol) of tetramethylethylenediamine (TMEDA) are introduced into a 1 liter round-bottomed flask.
The mixture is stirred at room temperature for 15 minutes and 23 g (190 mmol) of 2,3-dihydrobenzofuran are added.
The mixture is stirred for 4 hours at 35° C., cooled to -78° C. and 13.9 g (190 mmol) of dimethylformamide are added.
The temperature is allowed to return to 20° C., 500 ml of water are added and extraction is carried out with ethyl acetate (3*200 ml).
The organic phases are combined, dried and concentrated under vacuum.
The residue is purified by silica flash chromatography (elution: 5percent ethyl acetate in petroleum ether).
9.85 g (Yield: 35percent) of 7-formyl-2,3-dihydrobenzofuran are obtained--M.p.: 55° C.
Reference: [1] Patent: US6063810, 2000, A,
  • 7
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Reference: [1] Patent: US2008/255230, 2008, A1, . Location in patent: Page/Page column 10
  • 8
  • [ 496-16-2 ]
  • [ 68-12-2 ]
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Reference: [1] Patent: US2008/194650, 2008, A1, . Location in patent: Page/Page column 26
  • 9
  • [ 35700-40-4 ]
  • [ 79-22-1 ]
  • [ 196799-45-8 ]
Reference: [1] Patent: US2010/272681, 2010, A1,
  • 10
  • [ 35700-40-4 ]
  • [ 128625-52-5 ]
  • [ 4490-81-7 ]
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Reference: [1] Patent: US6011059, 2000, A,
  • 11
  • [ 35700-40-4 ]
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Reference: [1] Organic Letters, 2012, vol. 14, # 2, p. 556 - 559
[2] Patent: TW2016/2105, 2016, A,
[3] Patent: WO2008/82484, 2008, A1,
[4] Patent: WO2008/106139, 2008, A1,
  • 12
  • [ 608-33-3 ]
  • [ 196799-45-8 ]
Reference: [1] Advanced Synthesis and Catalysis, 2007, vol. 349, # 1-2, p. 193 - 203
[2] Tetrahedron Letters, 2000, vol. 41, # 14, p. 2269 - 2273
  • 13
  • [ 496-16-2 ]
  • [ 196799-45-8 ]
Reference: [1] Patent: US2008/255230, 2008, A1,
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