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Chemical Structure| 14631-43-7 Chemical Structure| 14631-43-7

Structure of 14631-43-7

Chemical Structure| 14631-43-7

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Product Details of [ 14631-43-7 ]

CAS No. :14631-43-7
Formula : C5H7NO
M.W : 97.12
SMILES Code : N#CC1CCCO1
MDL No. :MFCD07787008
InChI Key :RZZIKHSWRWWPAN-UHFFFAOYSA-N
Pubchem ID :4377949

Safety of [ 14631-43-7 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H311-H331
Precautionary Statements:P261-P280-P301+P310-P311
Class:6.1
UN#:2810
Packing Group:

Application In Synthesis of [ 14631-43-7 ]

* 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 [ 14631-43-7 ]
  • Downstream synthetic route of [ 14631-43-7 ]

[ 14631-43-7 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 91470-28-9 ]
  • [ 14631-43-7 ]
YieldReaction ConditionsOperation in experiment
62% With pyridine; trifluoroacetic anhydride In 1,4-dioxane; chloroform; ethyl acetate Preparation c-129
Tetrahydro-furan-2-carbonitrile
Trifluoroacetic anhydride (1.55 g, 7.38 mmol) was added slowly, with a rate of one drop every 10 seconds, to an ice-cold solution (0° C.) of tetrahydro-furan-2-carboxylic acid amide (0.77 g, 6.71 mmol) and pyridine (1.06 g, 13.42 mmol) in anhydrous 1,4-dioxane (10 mL).
The addition of trifluoroacetic anhydride was monitored to keep the internal temperature below 5° C. and was completed after 20 minutes.
The resulting mixture was allowed to warm to ambient temperature, and stirred for 3 hours.
Chloroform (100 mL) was added to the mixture, and then extracted with water (30 mL) and saturated aqueous sodium chloride (20 mL).
The organic extracts were dried (anhydrous magnesium sulfate), filtered, and concentrated in vacuo to give the crude product.
The residue was purified by flash column chromatography (hexanes to 25percent ethyl acetate/hexanes) to afford the title compound (0.51 g, 62percent) as a colorless oil. 1H NMR (CDCl3, 300 MHz): 4.70 (1H, m), 3.96 (2H, m), 2.24 (2H, m), 2.08 (2H, m).
62% With pyridine; trifluoroacetic anhydride In 1,4-dioxane at 5 - 20℃; for 3.33333 h; Trifluoroacetic anhydride (1. 55 g, 7. 38 MMOL) was added slowly, with a rate of one drop every 10 seconds, to an ice-cold solution (0 °C) of tetrahydro-furan-2- carboxylic acid amide (0. 77 g, 6. 71 MMOL) and pyridine (1. 06 g, 13. 42 MMOL) in anhydrous 1, 4-dioxane (10 mL). The addition of TRIFLUOROACETIC anhydride was monitored to keep the internal temperature below 5 °C and was completed after 20 minutes. The resulting mixture was allowed to warm to ambient temperature, and stirred for 3 hours. Chloroform (100 mL) was added to the mixture, and then extracted with water (30 mL) and saturated aqueous sodium chloride (20 mL). The organic extracts were dried (anhydrous magnesium sulfate), filtered, and concentrated IN VACUO to give the crude product. The residue was purified by flash column chromatography (hexanes to 25percent ethyl acetate/hexanes) to afford the title compound (0. 51 g, 62percent) as a colorless oil. H NMR (CDCI3, 300 MHz) : 4. 70 (1H, m), 3. 96 (2H, m), 2. 24 (2H, m), 2. 08 (2H, M).
References: [1] Patent: US2005/187266, 2005, A1, .
[2] Patent: WO2004/92145, 2004, A1, . Location in patent: Page 137.
  • 2
  • [ 38694-47-2 ]
  • [ 631-57-2 ]
  • [ 14631-43-7 ]
  • [ 1393708-93-4 ]
YieldReaction ConditionsOperation in experiment
34% With Candida antarctica lipase B; di-μ-oxo-di((S,S)-N,N'-bis((salicylaldehydo)ethylenediamine))dititanium(IV); water In toluene at 40℃; for 15 h; aq. buffer; Enzymatic reaction General procedure: Aldehyde (0.24 mmol) and (S,S)-[(salen)Ti(μ-O)]2 (5 mol percent) were dissolved in toluene (1 mL), and buffer (1 mL) and CALB (20 mg) were added. AcCN (3 equiv diluted to 250 μL with toluene) was added to the organic phase with a constant rate over 24-25 h using a syringe pump. The reaction was monitored by chiral GC using undecane (10 μL, 0.0473 mmol) as internal standard.
References: [1] Tetrahedron, 2012, vol. 68, # 37, p. 7680 - 7684.
  • 3
  • [ 4795-29-3 ]
  • [ 14631-43-7 ]
References: [1] Chemistry - A European Journal, 2016, vol. 22, # 15, p. 5156 - 5159.
[2] ACS Catalysis, 2013, vol. 3, # 7, p. 1652 - 1656.
  • 4
  • [ 109-99-9 ]
  • [ 172876-96-9 ]
  • [ 14631-43-7 ]
References: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 11, p. 1971 - 1975.
  • 5
  • [ 1608-67-9 ]
  • [ 7677-24-9 ]
  • [ 14631-43-7 ]
References: [1] Tetrahedron, 1983, vol. 39, # 6, p. 961 - 966.
[2] Tetrahedron, 1983, vol. 39, # 6, p. 967 - 974.
  • 6
  • [ 109-99-9 ]
  • [ 19158-51-1 ]
  • [ 14631-43-7 ]
References: [1] Organic Letters, 2011, vol. 13, # 21, p. 5928 - 5931.
[2] Synthesis (Germany), 2013, vol. 45, # 7, p. 874 - 887.
  • 7
  • [ 13369-70-5 ]
  • [ 7677-24-9 ]
  • [ 14631-43-7 ]
References: [1] Tetrahedron, 1983, vol. 39, # 6, p. 961 - 966.
  • 8
  • [ 13436-45-8 ]
  • [ 7677-24-9 ]
  • [ 14631-43-7 ]
  • [ 86172-03-4 ]
References: [1] Tetrahedron, 1983, vol. 39, # 6, p. 967 - 974.
  • 9
  • [ 924899-41-2 ]
  • [ 7677-24-9 ]
  • [ 14631-43-7 ]
References: [1] Advanced Synthesis and Catalysis, 2006, vol. 348, # 1-2, p. 118 - 124.
  • 10
  • [ 23247-31-6 ]
  • [ 14631-43-7 ]
References: [1] Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 565 - 570.
  • 11
  • [ 1148-11-4 ]
  • [ 14631-43-7 ]
References: [1] Chemical Science, 2017, vol. 8, # 3, p. 1790 - 1800.
  • 12
  • [ 172876-96-9 ]
  • [ 1148-11-4 ]
  • [ 14631-43-7 ]
  • [ 119020-06-3 ]
References: [1] Chemical Science, 2017, vol. 8, # 3, p. 1790 - 1800.
  • 13
  • [ 109-99-9 ]
  • [ 14631-43-7 ]
References: [1] Chimia, 2017, vol. 71, # 4, p. 226 - 230.
  • 14
  • [ 91470-28-9 ]
  • [ 1191-99-7 ]
  • [ 14631-43-7 ]
References: [1] Journal of the Chemical Society, 1945, p. 52[2] Journal of the American Chemical Society, 1947, vol. 69, p. 3002,3003.
  • 15
  • [ 23247-31-6 ]
  • [ 127-09-3 ]
  • [ 108-24-7 ]
  • [ 14631-43-7 ]
References: [1] Chemische Berichte, 1927, vol. 60, p. 2511.
  • 16
  • [ 23247-31-6 ]
  • [ 127-09-3 ]
  • [ 64-19-7 ]
  • [ 14631-43-7 ]
References: [1] Chemische Berichte, 1927, vol. 60, p. 2511.
 

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