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Chemical Structure| 54166-15-3 Chemical Structure| 54166-15-3

Structure of 54166-15-3

Chemical Structure| 54166-15-3

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Product Details of [ 54166-15-3 ]

CAS No. :54166-15-3
Formula : C17H22O5
M.W : 306.35
SMILES Code : C1=CC=CC=C1COC2CC(C2)(C(=O)OCC)C(=O)OCC
MDL No. :MFCD07700259
InChI Key :OSQKNXLJUGYQHW-UHFFFAOYSA-N
Pubchem ID :12815110

Safety of [ 54166-15-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 54166-15-3 ]

* 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.

  • Upstream synthesis route of [ 54166-15-3 ]
  • Downstream synthetic route of [ 54166-15-3 ]

[ 54166-15-3 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 54166-15-3 ]
  • [ 99974-66-0 ]
YieldReaction ConditionsOperation in experiment
91.5% With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; Compound diethyl 3-benzyloxy-cyclobutane-1,1-dicarboxylate(2 g) was dissolved in EtOH (100 ml), and 10 percent Pd/C(400 mg, 20 percent eq.) was added. The suspension was hydrogenated at room temperature overnight. The product was evaporated under reduced pressure (1.3 g, 91.5 percent yield). 1H NMR (400 MHz, CDCl3, d): 2.44–2.49, 2.85–2.90(2 m, 4H), 4.35–4.37 (m, 1H), 4.21 (q, J = 7.2 Hz, 4H), 1.26 (t, J = 10.8 Hz, 6H).
72% With hydrogen In ethanol for 3 h; A solution of benzyl ether Ic (3.0 g) in 60 mL of ethanol was treated with palladium dihydroxide (20 molpercent, 1.37 g of 20percent Pd(OH)2 on carbon). The mixture was hydrogenated at 50 psi for 3 h and then diluted with dichloromethane (200 mL). The solids were removed by filtration through a pad of celite. The filtrate was concentrated in rotavap and the product was purified on silica gel (Biotage 40-M column; gradient: 0 to 40percent ethyl acetate in hexanes) to afford the product (1.52 g; 72 percent) as a colorless oil.
64% With hydrogen In ethanol at 20℃; for 3.5 h; To a solution of compound BB2-b (40 g) in EtOH (500 mL) was added 10 percent palladium on charcoal (4 g) and the mixture was hydrogenated for 3.5 hours at 50 psi at room temperature. The catalyst was removed by filtration, washed with ethyl acetate, EtOH and the solvent was then removed under reduced pressure. The residue was purified by silica gel chromatography with hexane/ ethyl acetate as eluent to provide the title compound. TLC system; Petroleum ether: ethyl acetate (9:1), RF = 0.3. Yield: 18 g, 64 percent.
64% With hydrogen In ethanol at 20℃; for 3.5 h; Step c) Diethyl 3-hydroxycvclobutane-lJ-dicarboxylate (BB2-c)To a solution of compound BB2-b (40 g) in EtOH (500 mL) was added 10 percent palladium on charcoal (4 g) and the mixture was hydrogenated for 3.5 hours at 50 psi at room temperature. The catalyst was removed by filtration, washed with ethyl acetate, EtOH and the solvent was then removed under reduced pressure. The residue was purified by silica gel chromatography with hexane/ ethyl acetate as eluent to provide the title compound. TLC system; Petroleum ether: ethyl acetate (9: 1), RF = 0.3. Yield: 18 g, 64 percent.
64% With hydrogen In ethanol at 20℃; for 3.5 h; To a solution of compound BB2-b (40 g) in EtOH (500 mL) was added 10 percent palladium on charcoal (4 g) and the mixture was hydrogenated for 3.5 hours at 50 psi at room temperature. The catalyst was removed by filtration, washed with ethyl acetate, EtOH and the solvent was then removed under reduced pressure. The residue was purified by silica gel chromatography with hexane/ ethyl acetate as eluent to provide the title compound. TLC system; Petroleum ether: ethyl acetate (9: 1), RF = 0.3. Yield: 18 g, 64 percent.
64% With hydrogen In ethanol at 20℃; for 3.5 h; Step c) Diethyl 3 -hydroxy cyclo butane- 1 , 1-dicarboxylate (BB2-c) To a solution of compound BB2-b (40 g) in EtOH (500 mL) was added 10 percent palladium on charcoal (4 g) and the mixture was hydrogenated for 3.5 hours at 50 psi at room temperature. The catalyst was removed by filtration, washed with ethyl acetate, EtOH and the solvent was then removed under reduced pressure. The residue was purified by silica gel chromatography with hexane/ ethyl acetate as eluent to provide the title compound. TLC system; Petroleum ether: ethyl acetate (9: 1), RF = 0.3. Yield: 18 g, 64 percent.
64% With hydrogen In ethanol at 20℃; for 3.5 h; Step c) Diethyl 3-hydroxycvclobutane-1 ,1-dicarboxylate (BB2-c)To a solution of compound BB2-b (40 g) in EtOH (500 mL) was added 10 percent palladium on charcoal (4 g) and the mixture was hydrogenated for 3.5 hours at 50 psi at room temperature. The catalyst was removed by filtration and the filter washed with ethyl acetate and EtOH. The solvents were removed under reduced pressure and theafforded residue was purified by silica gel chromatography eluted with hexane/ EtOAc, which gave the title compound (18 g, 64 percent).

References: [1] Research on Chemical Intermediates, 2015, vol. 41, # 11, p. 8725 - 8733.
[2] Synthesis (Germany), 2012, vol. 44, # 13, p. 2091 - 2101.
[3] Patent: WO2009/8913, 2009, A2, . Location in patent: Page/Page column 60.
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 7, p. 2151 - 2155.
[5] Patent: WO2010/70615, 2010, A1, . Location in patent: Page/Page column 28; 29.
[6] Patent: WO2011/70539, 2011, A1, . Location in patent: Page/Page column 24-25.
[7] Patent: WO2011/70541, 2011, A1, . Location in patent: Page/Page column 24.
[8] Patent: WO2011/158197, 2011, A1, . Location in patent: Page/Page column 30.
[9] Patent: WO2012/172473, 2012, A1, . Location in patent: Page/Page column 21.
[10] Chemische Berichte, 1957, vol. 90, p. 1424,1427.
[11] Journal of Medicinal Chemistry, 1990, vol. 33, # 10, p. 2905 - 2915.
[12] Patent: WO2004/99224, 2004, A1, . Location in patent: Page/Page column 12-14.
[13] Inorganic Chemistry, 2012, vol. 51, # 19, p. 10317 - 10324.
[14] Chemistry - A European Journal, 2012, vol. 18, # 45, p. 14276 - 14281.
[15] Chemistry - A European Journal, 2014, vol. 20, # 46, p. 15216 - 15225.
[16] Patent: US2013/59846, 2013, A1, . Location in patent: Paragraph 0543-0551.
  • 2
  • [ 54166-15-3 ]
  • [ 84182-59-2 ]
References: [1] Collection of Czechoslovak Chemical Communications, 1982, vol. 47, # 9, p. 2440 - 2447.
 

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