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Chemical Structure| 5463-97-8 Chemical Structure| 5463-97-8

Structure of 5463-97-8

Chemical Structure| 5463-97-8

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Product Details of [ 5463-97-8 ]

CAS No. :5463-97-8
Formula : C12H14O3
M.W : 206.24
SMILES Code : O=C(O)C(C1(O)CCC1)C2=CC=CC=C2
MDL No. :MFCD24483360
InChI Key :AAEQHELGUQCYGL-UHFFFAOYSA-N
Pubchem ID :228406

Safety of [ 5463-97-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H332
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501

Application In Synthesis of [ 5463-97-8 ]

* 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 [ 5463-97-8 ]

[ 5463-97-8 ] Synthesis Path-Downstream   1~6

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  • [ 55930-34-2 ]
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  • [ 1191-95-3 ]
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  • [ 103-82-2 ]
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  • [ 5463-97-8 ]
YieldReaction ConditionsOperation in experiment
73% To a dried 250 mL round bottom flask containing 2 M lithium diisopropyl amide in THF (2 eq.) in THF (60 mL) at 0 C, was added phenyl acetic acid (l .Og, 7.35mmol, 1 eq). The resulting mixture was stirred at ambient temperature for 30 minutes. The reaction mixture was then cooled to -78C and a mixture of cyclobutanone (commercially available from Sigma- Aldrich, Milwaukee, WI) (0.617 g, 8.82 mmol, 1.2 eq.) in THF (20 mL) was added dropwise. The resulting mixture was then stirred at -78C and then at ambient temperature for 3 hours. Reaction progress was monitored by TLC (TLC eluent: 30 % EtOAc in hexane). The reaction mixture was poured into an EtO Ac/water mixture and the aqueous layer was extracted with EtOAc. The aqueous layer was then acidified with dilute hydrochloric acid and extracted with DCM. The DCM solution was washed with brine and concentrated. The residue was purified by column chromatography using silica gel eluting with 15 % EtOAc in hexane to yield 2-(l-hydroxycyclobutyl)-2-phenylacetic acid (1.1 g, 73%). lH NMR (300 MHz, CDC13) δ: 7.42 - 7.26 (m, 5H), 3.88 (s, 1H), 2.24-2.19 (m, 2H), 2.10-2.05 (m, 2H), 1.93 - 1.87 (m, 3H). m/z (ESI) 189 (M+H)+ (-Dehydroxy mass observed).
  • 4
  • [ 5463-97-8 ]
  • [ 1456507-20-2 ]
YieldReaction ConditionsOperation in experiment
73% With diphenylphosphoranyl azide; triethylamine; In toluene; at 120℃; for 12.0h; Into a 100 mL round bottom flask charged with 2-(l- hydroxycyclobutyl)-2-phenylacetic acid (0.5 g, 2.42 mmol, 1 eq.) in toluene (30 mL) were added TEA (2.5 eq) and diphenyl phosphoryl azide (2 eq). The resulting mixture was stirred at 120C for 12 hours. Reaction progress was monitored by TLC (TLC eluent: 30 % EtOAc in hexane). The reaction mixture was cooled and toluene was evaporated under reduced pressure to afford the initial product. The initial product was purified by column chromatography using silica gel eluting with 10% EtOAc in hexane to afford 8-phenyl-5-oxa-7-azaspiro[3.4]octan-6-one (0.5 g, 73%). lH NMR (300 MHz, CDC13) δ: 7.52 - 7.23 (m, 5H), 5.72 (s, 1H), 4.74 (s, 1H), 2.69-2.50 (m, 1H), 2.30-2.40 (m, lH), 2.10-2.20 (m, 1H), 1.94 - 1.66 (m, 1H), 1.75 - 1.64 (m, 1H), 1.43 - 1.35 (m, 1H).
  • 5
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  • [ 1456505-12-6 ]
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  • [ 5463-97-8 ]
  • [ 40297-26-5 ]
 

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Technical Information

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