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[ CAS No. 4653-11-6 ]

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CAS No. :4653-11-6 MDL No. :MFCD00005463
Formula : C8H10O2S Boiling Point : 296.9°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :170.23 g/mol Pubchem ID :78386
Synonyms :

Safety of [ 4653-11-6 ]

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

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  • Upstream synthesis route of [ 4653-11-6 ]
  • Downstream synthetic route of [ 4653-11-6 ]

[ 4653-11-6 ] Synthesis Path-Upstream   1~12

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YieldReaction ConditionsOperation in experiment
90% at 20℃; for 12 h; Inert atmosphere General procedure: A 10 mL glass vial with a screw cap was charged with 3-phenoxypropanoic acid 5a (0.75 mmol, 1.0 equiv), TFAA (2.25 mmol, 3 equiv) and TFA (0.8 mL). The reaction mixture was stirred at room temperature for 12 h and monitored by TLC or GC-MS. Upon completion, the solvent was removed under reduced pressure and the residue was subjected to silica gel flash column chromatography (hexanes : AcOEt) to give ketone product 6a.
76% at 100℃; for 0.0833333 h; Example 5.; Preparation of dichloror6,6'-bis(dimethylsilanediyl)di(η5-(7-phenyl-5,6-dihvdro-4/-/- indeno[5,4-.pound.>1thiophene-6-yl)1zirconium.; The preparation is described in the following scheme. KOH 6,7-dihydro-1-benzothiophen-4(5/-/)-one was obtained with an overall yield of 43percent via the acylation of thiophene by succinic anhydride followed by reduction of the ketone formed and by the cyclisation of 4-(2-thienyl)butanoic acid in the presence of the laton's reagent. Next, 4,5,5a,6-tetrahydro-7/-/-indeno[5,4-ιb]thiophen-7-one was synthesised from 6,7-dihydro-1 -benzothiophen-4(5H)-one with an overall yield of 30percent. The latter product was further reacted with one equivalent of PhLi in ether followed by acidification of the reaction medium to give a mixture of 7-phenyl-5,5a- dihydro-4H-indeno[5,4-ib]thiophene and 7-phenyl-5,8-dihydro-4H-indeno[5,4- .pound.>]thiophene as shown in the scheme belowThe lithium salt of this ligand was treated with 0.5 eqv of Me2SiCl2 in THF to form the respective ιb/s(cyclopentadienyl)dimethylsilane. This b/s-cyclopentadienyl ligand was isolated as a mixture of the Me2Si-bhdging ligands involving ca. 70percent of the desired isomers with a yield of 17percent by repeating flash chromatography on Silica Gel 60. It was metallated with 2 eqv of "BuLi in toluene-hexanes, and then with metallic salt ZrCI4(THF)2. This mixture was stirred overnight at room temperature and then filtered through glass frit. Crystals precipitated from the filtrate at a temperature of -3O0C were collected and dried in vacuum. On the evidence of 1H NMR spectroscopy, this product isolated with a yield of 13percent is a mixture of me- and meso-complexes in a ratio of 1 to 5. This 1H NMR spectrum is shown in figure 9. The meso-isomer was characterised by X-ray crystal structure analysis. Figure 10 is the ORTEP representation of the molecular structure of this meso-complex with thermal ellipsoids drawn at the 50percent probability level.The key geometric paramerers of this structure are:- bond lengths Zr-Cp(c) and Zr-Cp(c)' are 2.239(1 ) Angstroms;- angle between two cyclopentadienyl planes is 59.2°.
72% With phosphoric acid; acetic anhydride In water at 120℃; for 2.5 h; Ortho-phosphoric acid (85percent, 0.27 ml, 3.7 mmol) is dissolved in acetic acid anhydride (13 ml) and after addition of 4-thiophen-2-yl-butyric acid (9 g, 52.9 mmol) the mixture is stirred at 120°C for 2.5 h. The brown solution is cooled down using an ice bath, water is added and the reaction mixture is extracted with dichloromethane. The organic layers are washed with 2M NaOH solution and twice with water until a neutral pH is reached. The solution is dried over Na2SO4 and evaporated under reduced pressure. The crude product is obtained as a brown oil (7.84 g), which is further purified by flash-chromatography (silica gel, ethyl acetate /hexane 9: 1). Yield : 5.83 g (72percent) of a slightly yellow solid. MS (ESI) : 152 [M] +, 1 H-NMR (DMSO-d6) : o (ppm) 7.38 (d, 1H), 7.25 (d, 1H), 3.03 (t, 2H), 2.48 (m, 2H), 2.12 (t, 2H).
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 10, p. 869 - 872
[2] Tetrahedron Letters, 2003, vol. 44, # 21, p. 4007 - 4010
[3] Heterocycles, 1996, vol. 43, # 1, p. 127 - 131
[4] Patent: WO2010/76188, 2010, A1, . Location in patent: Page/Page column 17-19
[5] Patent: WO2005/77932, 2005, A2, . Location in patent: Page/Page column 208
[6] Archiv der Pharmazie, 1988, vol. 321, # 10, p. 735 - 738
[7] European Journal of Medicinal Chemistry, 1998, vol. 33, # 11, p. 867 - 877
[8] Journal of Medicinal Chemistry, 1985, vol. 28, # 12, p. 1886 - 1896
[9] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 5, p. 334 - 338
[10] Bulletin de la Societe Chimique de France, 1953, p. 62,68, 713, 717
[11] Journal of the American Chemical Society, 1935, vol. 57, p. 1611,1614
[12] Patent: US5756529, 1998, A,
[13] Patent: US5760068, 1998, A,
[14] Chemistry Letters, 2008, vol. 37, # 3, p. 320 - 321
[15] European Journal of Medicinal Chemistry, 2013, vol. 69, p. 490 - 497
[16] Patent: WO2015/95261, 2015, A1, . Location in patent: Page/Page column 100
[17] Patent: WO2015/89842, 2015, A1, . Location in patent: Page/Page column 99
[18] Organic Letters, 2015, vol. 17, # 21, p. 5484 - 5487
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  • [ 13414-95-4 ]
  • [ 74458-89-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1185 - 1193
[2] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 1, p. 87 - 92
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  • [ 4653-11-6 ]
  • [ 108-24-7 ]
  • [ 13414-95-4 ]
  • [ 74458-89-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1185 - 1193
[2] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 1, p. 87 - 92
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  • [ 13414-95-4 ]
  • [ 74458-90-5 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 1, p. 87 - 92
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  • [ 123-62-6 ]
  • [ 13414-95-4 ]
  • [ 74459-08-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, # 1, p. 87 - 92
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YieldReaction ConditionsOperation in experiment
85%
Stage #1: With hydrazine hydrate; potassium hydroxide In ethylene glycol at 180℃; for 10 h;
Stage #2: With hydrogenchloride In water
4-(Thiophen-2-yl)butanoic acidHydrazine hydrate (99percent) (2.2 Ml, 45.9 mmol) and KOH pellets (2.37 g, 42.4 mmol) were added to a solution of 4-oxo-4-(thiophen-2-yl)butanoic acid (2.3 g, 12.48 mmol) in ethylene glycol (30 Ml), and the reaction mixture was heated to 180 °C for 10 h. The reaction mixture was cooled to room temperature and diluted with water. The aqueous layer was washed with diethyl ether, acidified with 6N HCI and then extracted with diethyl ether. The organic layer was then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluant 2percent MeOH in CH2CI2), to get 4-(thiophen-2-yl)butanoic acid (1 .8 g, yield 85percent). 1H NMR (300 MHz, DMSO-d6) δ 12.06 (s, 1 H), 7.31 - 7.29 (m, 1 H), 6.94 - 6.91 (m, 1 H), 6.84 - 6.82 (m, 1 H), 2.82 - 2.77 (t, J = 7.7 Hz, 2H), 2.27 - 2.22 (t, J = 7.3 Hz, 2H), 1 .86 - 1.76 (m, 2H). MS (ESI) m/z: Calculated for C8H10O2S: 170.04; found: 170.8 (M+H)+
73% With potassium hydroxide; hydrazine In ethylene glycol for 8 h; Reflux Example 5.; Preparation of dichloror6,6'-bis(dimethylsilanediyl)di(η5-(7-phenyl-5,6-dihvdro-4/-/- indeno[5,4-.pound.>1thiophene-6-yl)1zirconium.; The preparation is described in the following scheme. KOH 6,7-dihydro-1-benzothiophen-4(5/-/)-one was obtained with an overall yield of 43percent via the acylation of thiophene by succinic anhydride followed by reduction of the ketone formed and by the cyclisation of 4-(2-thienyl)butanoic acid in the presence of the laton's reagent. Next, 4,5,5a,6-tetrahydro-7/-/-indeno[5,4-ιb]thiophen-7-one was synthesised from 6,7-dihydro-1 -benzothiophen-4(5H)-one with an overall yield of 30percent. The latter product was further reacted with one equivalent of PhLi in ether followed by acidification of the reaction medium to give a mixture of 7-phenyl-5,5a- dihydro-4H-indeno[5,4-ib]thiophene and 7-phenyl-5,8-dihydro-4H-indeno[5,4- .pound.>]thiophene as shown in the scheme belowThe lithium salt of this ligand was treated with 0.5 eqv of Me2SiCl2 in THF to form the respective ιb/s(cyclopentadienyl)dimethylsilane. This b/s-cyclopentadienyl ligand was isolated as a mixture of the Me2Si-bhdging ligands involving ca. 70percent of the desired isomers with a yield of 17percent by repeating flash chromatography on Silica Gel 60. It was metallated with 2 eqv of "BuLi in toluene-hexanes, and then with metallic salt ZrCI4(THF)2. This mixture was stirred overnight at room temperature and then filtered through glass frit. Crystals precipitated from the filtrate at a temperature of -3O0C were collected and dried in vacuum. On the evidence of 1H NMR spectroscopy, this product isolated with a yield of 13percent is a mixture of me- and meso-complexes in a ratio of 1 to 5. This 1H NMR spectrum is shown in figure 9. The meso-isomer was characterised by X-ray crystal structure analysis. Figure 10 is the ORTEP representation of the molecular structure of this meso-complex with thermal ellipsoids drawn at the 50percent probability level.The key geometric paramerers of this structure are:- bond lengths Zr-Cp(c) and Zr-Cp(c)' are 2.239(1 ) Angstroms;- angle between two cyclopentadienyl planes is 59.2°.
8 g With hydrazine hydrate; potassium hydroxide In diethylene glycol at 0℃; for 4 h; Reflux Compound 7 (12.0 g, 65.2 mmol) was dissolved in diethylene glycol (250 mL). Hydrazine monohydrate (7.18 g, 143 mmol) and KOH (8.05 g, 143 mmol) were added at 0 °C and the reaction mixture was heated to reflux for 4 h. The reaction mixture was cooled to rt, acidified to pH 2 by addition of 10 M HCl and extracted with CH2Cl2 (3 * 500 mL). The organic layer was dried (Na2SO4), concentrated in vacuum and the residue was purified by fc (dichloromethane/MeOH = 98/2, Ø = 5 cm, h = 30 cm, Rf = 0.32). Colorless liquid, yield 8.0 g, (72percent). Purity: 94percent, tR = 14.3 min. FT-IR (neat): ν (cm-1) = 2936 (O-H), 1701 (HOC=O). Exact mass (ESI): m/z = calcd. for (C8H10O2S)H 171.0402, found 171.0408. 1H NMR (CDCl3): δ (ppm) = 1.95 (quint, J = 7.4 Hz, 2H, CH2CH2CH2CO2H), 2.34 (t, J = 7.4 Hz, 2H, CH2CH2CH2CO2H), 2.82 (t, J = 7.4 Hz, 2H, CH2CH2CH2CO2H), 6.72 (dd, J = 3.5/1.1 Hz, 1H, 3-CH), 6.84 (dd, J = 5.1/3.5 Hz, 1H, 4-CH), 7.05 (dd, J = 5.1/1.1 Hz, 1H, 5-CH), 10.7 (bs, 1H, CO2H). 13C NMR (CDCl3): δ (ppm) = 26.5 (1C, CH2CH2CH2CO2H), 29.0 (1C, CH2CH2CH2CO2H), 33.1 (1C, CH2CH2CH2CO2H), 123.4 (1C, C-3), 124.6 (1C, C-4), 126.8 (1C, C-5), 143.8 (1C, C-2), 179.9 (1C, CO2H).
Reference: [1] European Journal of Medicinal Chemistry, 1998, vol. 33, # 11, p. 867 - 877
[2] Patent: WO2011/88187, 2011, A1, . Location in patent: Page/Page column 60-61
[3] Patent: WO2010/76188, 2010, A1, . Location in patent: Page/Page column 17-19
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1185 - 1193
[5] Archiv der Pharmazie, 1988, vol. 321, # 10, p. 735 - 738
[6] Journal of the American Chemical Society, 1935, vol. 57, p. 1611,1614
[7] Journal of the American Chemical Society, 1951, vol. 73, p. 5240,5241
[8] Journal of the Chemical Society, 1954, p. 4162,4165
[9] Bulletin de la Societe Chimique de France, 1953, p. 62,68, 713, 717
[10] Journal of Organic Chemistry, 1949, vol. 14, p. 802,809
[11] Tetrahedron Letters, 1984, vol. 25, # 47, p. 5439 - 5440
[12] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 5, p. 334 - 338
[13] European Journal of Medicinal Chemistry, 2009, vol. 44, # 8, p. 3147 - 3157
[14] European Journal of Medicinal Chemistry, 2013, vol. 69, p. 490 - 497
[15] Patent: WO2015/95261, 2015, A1, . Location in patent: Page/Page column 100
[16] Patent: WO2015/89842, 2015, A1, . Location in patent: Page/Page column 99
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Reference: [1] Journal of Organic Chemistry, 1994, vol. 59, # 23, p. 7072 - 7084
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Reference: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 1066
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Reference: [1] Journal of Organic Chemistry, 1994, vol. 59, # 23, p. 7072 - 7084
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Reference: [1] Chemistry - A European Journal, 1999, vol. 5, # 3, p. 937 - 950
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Reference: [1] Bulletin de la Societe Chimique de France, 1953, p. 62,68, 713, 717
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Reference: [1] Bulletin de la Societe Chimique de France, 1953, p. 62,68, 713, 717
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