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[ CAS No. 285-69-8 ]

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2D
Chemical Structure| 285-69-8
Chemical Structure| 285-69-8
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Product Details of [ 285-69-8 ]

CAS No. :285-69-8MDL No. :MFCD00800639
Formula : C4H6O2 Boiling Point : 128°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :86.09Pubchem ID :67511
Synonyms :

Computed Properties of [ 285-69-8 ]

TPSA : 21.8 H-Bond Acceptor Count : 2
XLogP3 : -0.4 H-Bond Donor Count : 0
SP3 : 1.00 Rotatable Bond Count : 0

Safety of [ 285-69-8 ]

Signal Word:DangerClass:3
Precautionary Statements:P501-P240-P210-P233-P243-P241-P242-P280-P370+P378-P303+P361+P353-P403+P235UN#:1993
Hazard Statements:H225Packing Group:
GHS Pictogram:

Application In Synthesis of [ 285-69-8 ]

  • Upstream synthesis route of [ 285-69-8 ]
  • Downstream synthetic route of [ 285-69-8 ]

[ 285-69-8 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 285-69-8 ]
  • [ 453-20-3 ]
Reference: [1] Journal of the Chemical Society, 1959, p. 248,254
  • 2
  • [ 1708-29-8 ]
  • [ 285-69-8 ]
YieldReaction ConditionsOperation in experiment
84.6% With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran at 0 - 20℃; Step 1 : To the solution of 24a (5.04g, 0.072mol) in 15OmL of DCM was added 85percent mCPBA(18.86g, 0.093mol) at O0C using ice-water bath. The mixture was stirred over weekend at r.t. and the precipitate was filtered off. The filtrated was washed successfully with saturated aqueous NaH CO3, water and brine. The organic layer was dried over anhydrous Na2SO4 and concentrated to give a mixture of white solid and yellow oil (5.24g, 84.6percent).
84.6% With mCPHA In dichloromethane at 0 - 20℃; Example 24 Preparation of 5-[5-Fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (4-hydroxy-tetrahydro-furan-3-yl)-amide Preparation of 4-Amino-tetrahydro-furan-3-ol Step 1: To the solution of 24a (5.04 g, 0.072 mol) in 150 mL of DCM was added 85percent mCPHA(18.86 g, 0.093mol) at 0° C. using ice-water bath. The mixture was stirred over weekend at r.t. and the precipitate was filtered off. The filtrated was washed successfully with saturated aqueous NaHCO3, water and brine. The organic layer was dried over anhydrous Na2SO4 and concentrated to give a mixture of white solid and yellow oil (5.24 g, 84.6percent).
66% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 48 h; 2,4-Dihydrofuran (7) (5.3 mL, 71.3 mmol) was added to a 500 mL round bottom flask containing CH2Cl2 (250 mL).
mCPBA was added and the solution stirred at ambient temperature for two days.
The solution was washed twice with aqueous Na2S2O3, then sat.
Na2CO3 and dried over Na2SO4.
The organic layer was then concentrated to afford the epoxide as a colorless oil (3.7 g, 66percent).
57% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 15 h; Reflux To a solution of 2,5-dihydrofuran SM 1 (5.0 g, 71 mmol) in DCM (100 mL) was added mCPBA (18.9 g, 109 mmol) at 0 °C, then the reaction mixture was stirred at reflux for 15 h. Quenched with water and extracted with EtOAc, dried and evaporated to give compound 1 (3.5 g, 57percent).

Reference: [1] Patent: WO2008/33562, 2008, A2, . Location in patent: Page/Page column 53
[2] Patent: US2009/76005, 2009, A1, . Location in patent: Page/Page column 23
[3] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8467 - 8487
[4] Patent: US5374416, 1994, A,
[5] Patent: US2009/30212, 2009, A1, . Location in patent: Page/Page column 15-16
[6] Patent: US6362343, 2002, B1, . Location in patent: Example 3
[7] Organic and Biomolecular Chemistry, 2009, vol. 7, # 9, p. 1921 - 1930
[8] Angewandte Chemie - International Edition, 2014, vol. 53, # 31, p. 8142 - 8145[9] Angew. Chem., 2014, vol. 126, # 31, p. 8280 - 8283,4
[10] Patent: WO2016/44770, 2016, A1, . Location in patent: Page/Page column 726
[11] Journal of the Chemical Society, 1959, p. 248,254
[12] Tetrahedron, 1993, vol. 49, # 28, p. 6263 - 6276
[13] Synthetic Communications, 2004, vol. 34, # 11, p. 1981 - 1987
[14] Patent: US5420343, 1995, A,
[15] Patent: US5602118, 1997, A,
[16] Patent: WO2012/101654, 2012, A2, . Location in patent: Page/Page column 66
[17] Patent: WO2013/138210, 2013, A1, . Location in patent: Paragraph 0173
[18] Patent: WO2015/52264, 2015, A1, . Location in patent: Paragraph 01202; 01203
  • 3
  • [ 285-69-8 ]
  • [ 144870-96-2 ]
YieldReaction ConditionsOperation in experiment
100% With ammonium hydroxide In isopropyl alcohol at 80℃; for 15 h; To a solution of compound 1 (0.3 g, 3.5 mmol) in isopropanol (5 mL) and ammonium hydroxide (10 mL) was stirred at 80 °C for 15 h. Quenched with water and extracted with EtOAc, dried and evaporated to give compound 2 (0.36 g, 100percent). LC-MS: m/z = 104.0 [M+H]
96.8% With ammonia; water In isopropyl alcohol at 80℃; for 18 h; Step 2: A mixture of crude 24b (300mg, 3.49mmol) obtained from last step, i- PrOH (3mL) and 26percent NH4OH (1OmL) was heated at a sealed tube at 800C for 18hs. A small amount of solid was filtered off and the filtrate was evaporated to give the crude 24c (0.348g, 96.8percent).
96.8% With ammonia In water; isopropyl alcohol at 80℃; for 18 h; Step 2: A mixture of crude 24b (300 mg, 3.49 mmol) obtained from last step, i-PrOH (3 mL) and 26percent NH4OH (10 mL) was heated at a sealed tube at 80° C. for 18 hs. A small amount of solid was filtered off and the filtrate was evaporated to give the crude 24c (0.348 g, 96.8percent).
Reference: [1] Patent: WO2016/44770, 2016, A1, . Location in patent: Page/Page column 726
[2] Patent: WO2008/33562, 2008, A2, . Location in patent: Page/Page column 53
[3] Patent: US2009/76005, 2009, A1, . Location in patent: Page/Page column 23
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