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[ CAS No. 33993-24-7 ] {[proInfo.proName]}

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Chemical Structure| 33993-24-7
Chemical Structure| 33993-24-7
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Product Details of [ 33993-24-7 ]

CAS No. :33993-24-7 MDL No. :MFCD12404941
Formula : C8H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :LZEPOJMTQYNFTR-UHFFFAOYSA-N
M.W : 154.16 Pubchem ID :297009
Synonyms :

Safety of [ 33993-24-7 ]

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 [ 33993-24-7 ]

* 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 [ 33993-24-7 ]

[ 33993-24-7 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 1759-53-1 ]
  • [ 33993-24-7 ]
YieldReaction ConditionsOperation in experiment
75% With dicyclohexyl-carbodiimide In dichloromethane for 24h;
With acetic anhydride
With tetrachloromethane; Hexamethylphosphorous triamide In tetrahydrofuran at -70℃;
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;
With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; 45 Preparation of 6; Cyclopropane carboxylic acid (29 g, 336.9 mmol, 1 eq) is dissolved in 500 mL of dry DCM. DCC (34.75 g, 168.5 mmol, 0.5 eq) is added to the solution at 0 °C as a solution in 100mL DCM dropwise over 0.5 hour. The reaction mixture is allowed to warm to rt and stirred overnight. The resulting slurry is filtered through a pad of celite, stripped, and dissolved in 500 mL of hexane, filtered through an additional pad of celite to remove the remaining byproducts and stripped. The resulting oil was vacuum distilled to yield the pure anhydride.
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; 31 [Example 31] To a solution of cyclopropanecarboxylic acid (80 mg, 0.929 mmol) in dichloromethane (1 mL), DCC (105 μL, 0.465 mmol) was added at room temperature. After stirring at room temperature for 24 hours, the reaction solution was diluted with cool hexane and filtrated through cotton plug. The resultant filtrate was distilled under reduced pressure for solvent removal to obtain a crude product of cyclopropanecarboxylic anhydride (141 mg).

  • 2
  • [ 33993-24-7 ]
  • [ 39217-08-8 ]
  • [ 156221-80-6 ]
  • 3
  • [ 33993-24-7 ]
  • [ 302964-24-5 ]
  • 2-[(Cyclopropylcarbonyl)amino]-N-(2-chloro-6-methylphenyl)-5-thiazolecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% In 1,4-dioxane; at 93℃; [0410] A solution of 315D (50.6 mg, 0.19 mmol) and cyclopropanecarboxylic acid anhydride (302 mg, 1.96 mmol) in dioxane (2 mL) was heated to 93 C. overnight. The mixture was concentrated in vacuo, diluted with EtOAc and washed with satd. Aq. KHCO3 solution (2×). The organic extract was dried (Na2SO4), filtered and concentrated. The residue was triturated with ether to obtain the title compound (11 mg, 17%) as a white solid.
  • 4
  • [ 33993-24-7 ]
  • [ 1631137-51-3 ]
  • [ 2135318-49-7 ]
YieldReaction ConditionsOperation in experiment
55% With triethylamine In dichloromethane at 20℃; for 2h;
  • 5
  • [ 33993-24-7 ]
  • [ 50-27-1 ]
  • (16α,17β)-16,17-dihydroxyestra-1(10),2,4-trien-3-yl cyclopropanecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: Estriol With sodium hydroxide In propan-1-ol for 0.166667h; Stage #2: cyclopropanecarboxylic anhydride With potassium hydrogencarbonate In propan-1-ol 5 Example 5 Example 5 (8xi,9xi,14xi,16α,17β)-16,17-dihydroxyestra-1(10),2,4-trien-3-yl cyclopropanecarboxylate (EC5105) 62.3 g of estriol (0.22 mol) was suspended in 2 propanol (1.5 L) and then 325 ml of 2 M NaOH (0.65 mol) was added, and the thick slurry was allowed to stir for ten minutes before addition of 1-cyclopropylcarboxlyic acid anhydride (100 g, 0.65 mol). The now homogenous mixture was then diluted with 4 L of 4% potassium bicarbonate and the resulting solids collected by vacuum filtration and the solids were allowed to dry on the filter overnight. The resulting solids were then crystallized from acetone-hexanes to produce the title compound. 1H NMR (δ, CDCl3, 300 MHz) 7.29-7.25 (m, 1H), 6.84 (dd, J=8.4, 2.4 Hz, 1H), 6.79 (d, J=2.4 Hz, 1H), 4.20-4.15 (m, 1H), 3.60 (t, J=4.8 Hz, 1 Hz), 2.88-2.82 (m, 2H), 2.35-2.23 (m, 2H), 0.80 (s, 3H). IR (cm-1): 3541, 3453, 3244, 1726, 1381, 1136, 1085, 1060, 885. Melting Point: 134-137° C.
  • 6
  • [ 33993-24-7 ]
  • [ 1093418-75-7 ]
  • methyl 4-bromo-2-(cyclopropanecarbonyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
83.39% Stage #1: methyl 4-bromo-2-iodobenzoate With isopropylmagnesium chloride lithium chloride In tetrahydrofuran at -78℃; for 0.5h; Stage #2: cyclopropanecarbonyl cyclopropanecarboxylate In tetrahydrofuran at -78 - 20℃; for 2h; 172 To a solution of methyl 4-bromo-2-iodobenzoate (1.6 g, 4.69 mmol) in THF (16.26 mL), a 2 M solution of isopropylmagnesium chloride in THF (2.58 mL, 5.16 mmol) was added dropwise at -78°C. After 30 minutes cyclopropanecarboxylic anhydride (0.67 mL, 6.1 mmol) was added at the same temperature. After addition was complete the reaction mixture was stirred at room temperature for 2 hours. It was then quenched with a saturated solution of ammonium chloride and extracted three times with EtOAc. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (KP silica gel, SNAP 340) eluting with a gradient of EtOAc in cyclohexane from 2% to 40% to give methyl 4-bromo-2-(cyclopropanecarbonyl)benzoate (1.108 g, 3.914 mmol, 83.39% yield) as a yellow oil.1H NMR (400 MHz, DMSO-d6) δ 1.05 - 1.14 (m, 4H), 2.40 (tt, J = 6.7, 5.5 Hz, 1H), 3.80 (s, 3H), 7.76 (dd, J = 8.2, 0.5 Hz, 1H), 7.80 - 7.89 (m, 2H). LC-MS (Method A): r.t.1.08 min. MS (ESI) m/z of product not observed due to poor ionization
83.39% Stage #1: methyl 4-bromo-2-iodobenzoate With isopropylmagnesium chloride lithium chloride In tetrahydrofuran at -78℃; for 0.5h; Stage #2: cyclopropanecarbonyl cyclopropanecarboxylate In tetrahydrofuran at -78 - 20℃; for 2h; 172 To a solution of methyl 4-bromo-2-iodobenzoate (1.6 g, 4.69 mmol) in THF (16.26 mL), a 2 M solution of isopropylmagnesium chloride in THF (2.58 mL, 5.16 mmol) was added dropwise at -78°C. After 30 minutes cyclopropanecarboxylic anhydride (0.67 mL, 6.1 mmol) was added at the same temperature. After addition was complete the reaction mixture was stirred at room temperature for 2 hours. It was then quenched with a saturated solution of ammonium chloride and extracted three times with EtOAc. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (KP silica gel, SNAP 340) eluting with a gradient of EtOAc in cyclohexane from 2% to 40% to give methyl 4-bromo-2-(cyclopropanecarbonyl)benzoate (1.108 g, 3.914 mmol, 83.39% yield) as a yellow oil.1H NMR (400 MHz, DMSO-d6) δ 1.05 - 1.14 (m, 4H), 2.40 (tt, J = 6.7, 5.5 Hz, 1H), 3.80 (s, 3H), 7.76 (dd, J = 8.2, 0.5 Hz, 1H), 7.80 - 7.89 (m, 2H). LC-MS (Method A): r.t.1.08 min. MS (ESI) m/z of product not observed due to poor ionization
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