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[ CAS No. 53090-46-3 ]

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Chemical Structure| 53090-46-3
Chemical Structure| 53090-46-3
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CAS No. :53090-46-3 MDL No. :MFCD07779220
Formula : C9H10O3S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :198.24 g/mol Pubchem ID :10535956
Synonyms :

Safety of [ 53090-46-3 ]

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:

Application In Synthesis of [ 53090-46-3 ]

  • Upstream synthesis route of [ 53090-46-3 ]
  • Downstream synthetic route of [ 53090-46-3 ]

[ 53090-46-3 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 1468-83-3 ]
  • [ 105-58-8 ]
  • [ 53090-46-3 ]
YieldReaction ConditionsOperation in experiment
47%
Stage #1: With sodium hydride In toluene for 0.5 h; Heating / reflux
Stage #2: With acetic acid In toluene at 0℃;
Example 1B10 11 12(wherein R1 is remaining moiety of the QA group, and R2 is the remaining moiety of the QB group in formula 1.0)Part A:To a mixture containing sodium hydride (18.6 g, 465 mmol) (60percent dispersion in mineral oil, washed with hexane to remove mineral oil) and diethyl carbonate (36 mL, 296 mmol) in toluene (200 mL) at reflux, was added 3-acetylthiophene (3) (18.7 g, 148 mmol) in toluene (60 mL) via dropwise addition using an addition funnel. After the addition was complete, the mixture was refluxed for an additional 30 minutes. The reaction mixture was then cooled to room temperature and placed in an ice bath, quenched with acetic acid (42 mL), water, and extracted with toluene. The combined toluene extracts were washed with water (x4), and brine, dried over magnesium sulfate and concentrated to give a brown oil which was subjected to vacuum distillation. The fraction boiling at approximately 1400C afforded compound 4 (13.8 g, 47 percent yield).
765 mg
Stage #1: With potassium <i>tert</i>-butylate In toluene at 65 - 80℃; for 0.5 h; Inert atmosphere
Stage #2: at 80℃; for 1.5 h;
In nitrogen atmosphere, diethyl carbonate 2.3 g of toluene 10 ml solution heated to 65 °C, addingtertButoxy potassium 875 mg, in the 65 °C stirring for 30 minutes. Raising the temperature to 80 °C after, dropping the 3 - acetyl thiophene 618 mg dissolved in toluene 5 ml of liquid, in the 80 °C stirring for 1.5 hours. Adding methanol to the room temperature, adding ethyl acetate, water, saturated salt water are successively washing, magnesium sulfate for drying. The resulting residue is purified by silica gel column chromatography, to obtain the title compound 765 mg.
4.2 g
Stage #1: With potassium <i>tert</i>-butylate In toluene at 60 - 65℃; for 0.5 h;
Stage #2: at 75 - 80℃; for 1.5 h;
Diethyl carbonate (9.36 g, 79.37 mmol) in toluene (50 ml) was heated to 60 °C. At thistemperature, potassium t-butoxide (7.11 g, 63.52 mmol) was added portionwise. Theresultant mixture was heated at 65 °C for half an hour. Then the reaction temperature wasraised to 75 °C, and 1-(thiophen-3-yl)ethanone (5 g, 39.7 mmol) was added dropwise. Thereaction mixture was heated to 80 °C for 90 min, and then allowed to cooled to roomtemperature. The precipitate solid was filtrated and washed thoroughly with ether. This solidwas dissolved in ethyl acetate, washed with brine, dried over Na2S04, filtered, andconcentrated under reduced pressure. The residue was purified by silica gel columnchromatography, eluting with PE/Et0Ac=5:1, to get the desired compound (4.2 g) as abrown oil. LC-MS (ESI+): m/z 199.0 (M+Ht
Reference: [1] Patent: WO2008/82490, 2008, A2, . Location in patent: Page/Page column 71
[2] Journal of Medicinal Chemistry, 1999, vol. 42, # 20, p. 4081 - 4087
[3] Organic Letters, 2016, vol. 18, # 20, p. 5408 - 5411
[4] Patent: CN108137513, 2018, A, . Location in patent: Paragraph 0173; 0174
[5] Patent: WO2018/125983, 2018, A1, . Location in patent: Page/Page column 67; 68
  • 2
  • [ 1468-83-3 ]
  • [ 53090-46-3 ]
YieldReaction ConditionsOperation in experiment
83%
Stage #1: With potassium <i>tert</i>-butylate In toluene at 60 - 65℃; for 0.5 h;
Stage #2: at 75 - 80℃; for 1.5 h;
PREPARATION 22; Ethyl 3-oxo-3-(3-thienyl)propionate; Diethyl carbonate (36.3 ml, 300 mmol) in toluene (18 ml) was heated to 60°C. At this temperature, potassium tert-butoxide (13.0 g, 120 mmol) was portionwise added and, once the addition was over, heated at 65°C for half an hour. Then the temperature is rawased to 75°C and 3-acethylthiophene (9.2g, 73 mmol) in toluene (18 ml) was dropwise added. The reaction mixture was heated at 80°C for 90 min, then allowed to reach room temperature and the precipitated solid was filtrated and washed thoroughly with ether. This solid was dissolved in water. After successive extractions with ethyl acetate, the organic phase was washed with brine and dried over sodium sulfate, filtered and evaporated. A dark oil was obtained (12.0 g, 83percent yield) as the desired final product. No. (CDCl3): 1.25 (t, 3H), 3.90 (s, 2H), 4.20 (q, 2H), 7.35 (m, 1H), 7.55 (m, 1H), 8.10 (m, 1H).
Reference: [1] Patent: WO2005/123693, 2005, A1, . Location in patent: Page/Page column 57-58
  • 3
  • [ 872-31-1 ]
  • [ 15226-74-1 ]
  • [ 6148-64-7 ]
  • [ 53090-46-3 ]
YieldReaction ConditionsOperation in experiment
86% With 1H-imidazole; palladium diacetate; triethylamine; [5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphane; magnesium chloride In tetrahydrofuran at 90℃; for 0.5 h; Microwave irradiation To a stirred mixture of aryl or heteroaryl halide(Br, I) (0.5 mmol), potassium mono ethyl malonate (0.75 mmol) in THF (10 mL) taken in a 30 mL microwave vial, was added Pd(OAc)2(5 molpercent), Xantphos (5 mol percent), MgCl2 (0.75), Et3N ( 0.75mmol), imidazole (1 mmol) followed by Co2(CO)8 (0.15mmol). The vial was sealed immediately and microwave irradiated at 90°C for 30min. The reaction mixture was concentrated and diluted with ethyl acetate and water. The ethyl acetate layer was separated, dried over sodium sulphate and concentrated. The crude product obtained was purified by column chromatography to get the pure compound.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 25, p. 3525 - 3528
  • 4
  • [ 41507-35-1 ]
  • [ 141-78-6 ]
  • [ 53090-46-3 ]
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 30, p. 10405 - 10409
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