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Structure of 58414-52-1

Chemical Structure| 58414-52-1

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Product Details of [ 58414-52-1 ]

CAS No. :58414-52-1
Formula : C7H8O2S
M.W : 156.20
SMILES Code : O=C(OC)CC1=CSC=C1
MDL No. :MFCD00052947
InChI Key :RZGRWVULDSXQSM-UHFFFAOYSA-N
Pubchem ID :94041

Safety of [ 58414-52-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P264-P270-P301+P312-P330

Application In Synthesis of [ 58414-52-1 ]

* 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 [ 58414-52-1 ]

[ 58414-52-1 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 67-56-1 ]
  • [ 6964-21-2 ]
  • [ 58414-52-1 ]
YieldReaction ConditionsOperation in experiment
100% With acetyl chloride; at 0 - 20℃; Acetyl chloride (7.50 ml, 106 mmol) was added dropwise to a solution of <strong>[6964-21-2]3-thiopheneacetic acid</strong> (5.00 g, 35.3 mmol) in dry MeOH (150 ml) at 0 C. The mixture was left to slowly reach room temperature and stirred overnight. Solvents were evaporated and residue filtered through a short plug of silica gel (DCM) to give a quantitative yield of the title compound as an oil. 1H NMR (400 MHz, CDCl3): δ 3.64 (s, 2H), 3.70 (s, 3H), 7.03-7.05 (m, 1H), 7.14-7.15 (m, 1H), 7.27-7.29 (m, 1H).
100% With acetyl chloride; at 0 - 20℃; Acteyl chloride (7.50 ml, 106 mmol) was added dropwise to a solution of <strong>[6964-21-2]3-thiopheneacetic acid</strong> (5.00 g, 35.3 mmol) in dry MeOH (150 ml) at 0 C. The mixture was left to slowly reach room temperature and stirred overnight. Solvents were evaporated and residue filtered through a short plug of silica gel (DCM) to give a quantitative yield of the title compound an oil. 1H MR (400 MHz, CDC13): 3.64 (s, 2H), 3.70 (s, 3H), 7.03-7.05 (m, 1H), 7.14 7.15 (m, 1H), 7.27-7.29 (m, 1H).
80% With sulfuric acid; at 0℃; for 14h;Reflux; To a stirred solution of 2-(thiophen3-yflacetic acid (5 g, 35.2 mmoi) in methanol (60 ml) at 0 cc was added drop wise solution of H2S04 (6.92 ml, 130 mmofl, The reaction mixture was refluxed for 1 4h, After completion of reaction, methanol was evaporated and residue was further diluted with dichioromethane, An organic layer was washed with saturated sodium bicarbonate solution and evaporated under reduced pressure to afford methyl 2-(thiophen-3-yl)acetate (4.4 g, 80%) as oil.
With sulfuric acid; for 24h;Reflux; [00165] Methyl thiophene-3-acetate LXXXIV (M3) was synthesized following the method reported by Kim, L. Chen, Gong, Y. Osada, Macromolecules 1999, 32, 3964- 3969, the disclosure of which is incorporated herein by reference in its entirety. Briefly, 3-Thiopheneacetic acid (8.52 g, 60 mmol) was dissolved in 50 mL of methanol with 2 drops of concentrated H2504. The mixture was heated in an oil bath and refluxed for 24 hours. After the removal of methanol, the crude product was redissolved in diethylether, washed with DI water and dried with anhydrous magnesium sulfate. Pure product was obtained after filtration and evaporation of solvent. The structure was analyzed and confirmed with ‘H NMR spectroscopy.
With thionyl chloride; at 0 - 68℃; for 12h; To a solution of 2-(3-thienyl)acetic acid (12.1, 5.40 g, 37.9 mmol, 1 equivalent) in MeOH (50 mL) was added thionyl chloride (6.78 g, 56.9 mmol, 4.13 mL, 1.5 equivalent) at 0 C. The mixture was heated to 68 C. for 12 hours. After this time, the reaction solution was evaporated and to this residue was added saturated sodium bicarbonate solution (80 mL). The suspension was extracted with ethyl acetate (35 mL*3), then dried over sodium sulfate and the solvent was removed to afford methyl 2-(thiophen-3-yl)acetate (12.2, 5.8 g, yield=93%) as a yellow oil without further purification.
With thionyl chloride; at 0 - 25℃; for 1h; To a solution of 2-(thiophen-3-yl)acetic (500 mg, 3.52 mmol) in MeOH (5 ml) at 0 C was added SOCl2 (1.02 ml, 14.07 mmol) and stirred at 25 C for 1 h. The RM was concentrated in vacuo to give methyl 2-(thiophen-3-yl)acetate as a yellow oil.1H NMR (400 MHz, MeOD) d 7.35 (dd, J = 5, 3 Hz, 1H), 7.21 (dd, J = 3, 1 Hz, 1H), 7.03 (dd, J = 5, 1 Hz, 1H), 3.69 (s, 3H), 3.63 (s, 2H).

  • 2
  • [ 6964-21-2 ]
  • [ 79-22-1 ]
  • [ 58414-52-1 ]
  • 3
  • [ 6964-21-2 ]
  • [ 58414-52-1 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 2 This Example illustrates the preparation of (E)-methyl 3-methoxy-2-(3-thienyl)propenoate (compound number 1 of Table II). Methyl 3-thienylacetate was prepared by heating 3-thienylacetic acid in acidic methanol. It is an oil, 1H nmr: delta 3.71 (2H,s), 3.76 (3H,s) ppm.
  • 4
  • [ 6964-21-2 ]
  • [ 18107-18-1 ]
  • [ 58414-52-1 ]
YieldReaction ConditionsOperation in experiment
Example 41 Preparation of methyl 2-(thiophen-3-yl)acetate (E41) To 2-(thiophen-3-yl)acetic acid in MeOH at 0 C. was added TMS-CH2N2. The solution was stirred for 3 hours then quenched with a few drops of AcOH. The solvents were evaporated. Column chromatography (SiO2, 3-15% EtOAc/Hex) gave pure methyl 2-(thiophen-3-yl)acetate (E41).
In methanol; at 0℃; for 3h; To 2-(thiophen-3-yl)acetic acid in MeOH at 0C was added TMS-CH2N2. The solution was stirred for 3 hours then quenched with a few drops of AcOH. The solvents were evaporated. Column chromatography (Si02, 3-15% EtO Ac/Hex) gave pure methyl 2- (thiophen-3-yl)acetate (E41).
 

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