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[ CAS No. 143140-39-0 ] {[proInfo.proName]}

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Chemical Structure| 143140-39-0
Chemical Structure| 143140-39-0
Structure of 143140-39-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 143140-39-0 ]

CAS No. :143140-39-0 MDL No. :MFCD12405321
Formula : C7H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 126.15 Pubchem ID :-
Synonyms :

Safety of [ 143140-39-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P301+P312-P330-P501 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
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Application In Synthesis of [ 143140-39-0 ]

* 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 [ 143140-39-0 ]

[ 143140-39-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 143140-39-0 ]
  • [ 25021-04-9 ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: methyl 2-cyclobutylideneacetate With lithium hydrochloride monohydrate; water at 20℃; Stage #2: With hydrogenchloride In water at 0℃; 40A Example 40ACyclobutylideneacetic acid 313 g (2.48 mol) of methyl cyclobutylideneacetate [prepared according to A. Goti et al., Tetrahedron 48 (25), 5283-5300 (1992)] are initially charged, a solution of 208 g (4.96 mol) of lithium hydroxide monohydrate in 4.38 liters of water is added at room temperature and the mixture is stirred at room temperature for 3.5 h. The mixture is then cooled to 0° C., and the pH is adjusted to 3.5 using concentrated hydrochloric acid. The product is then filtered off with suction, washed with a little cold water and dried under reduced pressure. This gives 213 g (76% of theory) of the title compound.1H-NMR (400 MHz, CDCl3): δ=11.80 (br. s, 1H), 5.61-5.58 (m, 1H), 3.14 (t, 2H), 2.85 (t, 2H), 2.10 (quin, 2H).MS (ESIpos): m/z=113 (M+H)+.
23% With lithium hydroxide monohydrate; water In methanol at 25℃; 134 Example 134 Preparation of 2-cyclobutylideneacetic acid Example 134 Preparation of 2-cyclobutylideneacetic acid To a solution of methyl 2-cyclobutylideneacetate (100 mg, 0.793 mmol) in MeOH (1.00 mL) stirring at RT was added 2N LiOH solution (prepared from lithium hydroxide hydrate (100 mg, 2.378 mmol) and water (1 mL)). The mixture was stirred at 25° C. overnight, then it was worked up by addition of 2N HCl and extracted with CH2Cl2. The combined organic layer was dried to give a white solid, which was purified by silica gel chromatography (0-70% EtOAc/hexane) to give the title compound as a white solid (20 mg, 23%): IR (thin film) 2923, 1647 cm-1; 1H NMR (400 MHz, CDCl3) δ 10.89 (s, 1H), 5.60 (dd, J=4.3, 2.1 Hz, 1H), 3.38-3.02 (m, 2H), 2.97-2.71 (m, 2H), 2.10 (dq, J=15.9, 8.0 Hz, 2H); 13C NMR (101 MHz, CDCl3) δ 172.35, 171.33, 112.13, 34.10, 32.58, 17.56.
23% With hydrogenchloride; lithium hydroxide In methanol; water at 20 - 25℃; 134 Preparation of 2-cyclobutylideneacetic acid Example 134 Preparation of 2-cyclobutylideneacetic acid To a solution of methyl 2-cyclobutylideneacetate (100 mg, 0.793 mmol) in MeOH (1.00 mL) stirring at RT was added 2N LiOH solution (prepared from lithium hydroxide hydrate (100 mg, 2.378 mmol) and water (1 mL)). The mixture was stirred at 25° C. overnight, then it was worked up by addition of 2N HCl and extracted with CH2Cl2. The combined organic layer was dried to give a white solid, which was purified by silica gel chromatography (0-70% EtOAc/hexane) to give the title compound as a white solid (20 mg, 23%): IR (thin film) 2923, 1647 cm-1; H NMR (400 MHz, CDCl3) δ 10.89 (s, 1H), 5.60 (dd, J=4.3, 2.1 Hz, 1H), 3.38-3.02 (m, 2H), 2.97-2.71 (m, 2H), 2.10 (dq, J=15.9, 8.0 Hz, 2H); 13C NMR (101 MHz, CDCl3) δ 172.35, 171.33, 112.13, 34.10, 32.58, 17.56.
Stage #1: methyl 2-cyclobutylideneacetate With methanol; sodium hydroxide; water Stage #2: With hydrogenchloride In methanol; water 1.2 Step 2: Cyclobutylidene acetic acidMethyl cyclobutylidene acetate was hydrolyzed in methanol: 2N NaOH (1:1). After neutralization with 6N HCl and extraction with ethyl acetate the desired acid was obtained as a white solid.
With lithium hydroxide 15.1a Synthesis of 2-cyclobutylideneacetic acid Detailed experimental procedure and analytical data is as follows.

  • 2
  • [ 683-98-7 ]
  • [ 143140-39-0 ]
  • C10H14F2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With zinc In tetrahydrofuran at 65℃; for 15h; 2 Example 2; Preparation of compound of formula Dissolve methyl difluorobromoacetate (75.6g, 0.40mol, 1.0eq.) In tetrahydrofuran (500mL),Compound of formula II (50.00g, 0.40mol, 1.0eq.) And zinc powder (26.2g, 0.40mol, 1.0eq.) Were added, and refluxed at 65 ° C for 15h,250mL of saturated ammonium chloride aqueous solution was added for liquid separation, and the organic phase was washed with saturated brine and dried.After concentration, 70.9 g of the compound of formula III was obtained with a yield of 75%.
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