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Chemical Structure| 20201-24-5 Chemical Structure| 20201-24-5

Structure of 20201-24-5

Chemical Structure| 20201-24-5

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Product Details of [ 20201-24-5 ]

CAS No. :20201-24-5
Formula : C7H12O3
M.W : 144.17
SMILES Code : CC(C)C(C(OCC)=O)=O
MDL No. :MFCD00009122
InChI Key :CKTYYUQUWFEUCO-UHFFFAOYSA-N
Pubchem ID :88406

Safety of [ 20201-24-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225
Precautionary Statements:P210-P403+P235
Class:3
UN#:3272
Packing Group:

Application In Synthesis of [ 20201-24-5 ]

* 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 [ 20201-24-5 ]

[ 20201-24-5 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 20201-24-5 ]
  • [ 3715-29-5 ]
YieldReaction ConditionsOperation in experiment
With lithium hydroxide; water; In tetrahydrofuran; at 20℃; Example 8 25. N-toluenesulfonyl-alpha-dehydrovaline.; To Ethyl 3-methyl-2-oxobutanoate, (15.0 g, 104.0 mmol) in THF (150 mL) was added LiOHNo.H2O(5.30 g, 125.0 mmol). This stirred at rt overnight, then the solvent was stripped. The resulting white solid was slurried in MTBE (150 mL) and cooled to 0 C, then HCI (12.1 N, 11.0 mL) was added. The resulting biphasic was warmed to rt, then saturated with Na2S04. The inorganic solids were filtered and washed with MTBE (50 mL). The combined organics were stripped to give a light yellow oil. This oil was dissolved in toluene (84 mL) and diethyleneglycol diethyl ether (12 mL) and p-toluenesulfonamide (14.2 g, 83.2 mmol) then methanesulfonic acid (0.54 mL, 8.3 mmol) were added. The resulting mixture was heated at reflux with Dean-Stark removal of water for 24h, then cooled to rt. The resulting mixture was mixed with EtOAc (45 mL) and NaHC03 (14.1 g) in water (150 mL). Upon complete C02 evolution and dissolution, the aqueous layer was separated, then the organics were washed with NaHC03 (1.6 g) in water (45 mL). The combined aqueous layers were washed with EtOAc (2 x 45 mL), then cooled to 0 C, and treated with HCl (12. IN, 15.4 mL), to give a white solid precipitate, which upon filtration and drying gave 15.0 g of crude material. This material was dissolved in MeOH (45 mL), then toluene (100 mL) was added. This was heated to 90 C, and the MeOH was removed. Then n-heptane (100 mL) was added slowly over 2h at 80 C, then cooled slowly to 0 C. Filtration gave 12.0 g of pure white material (54% yield). mp 188.5-189.5 C. IH-NMR (400 MHz, CD30D) d 7.67 (d, 2H, 20.1 Hz), 7.32 (d, 2H, 20.1 Hz), 2.42 (s, 3H), 2.09 (s, 3H), 1.79 (s, 3H); ¹3C NMR (100 MHz, DMSO-d6) 166.8,146.9,142.8,138.6,129.6, 126.9, 122.1, 22.1, 21.4, 21.3 ppm. HRMS calcd for C12H14N04S (M-H) : 268.0644, Found: 268.0638.
 

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