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Chemical Structure| 16847-90-8 Chemical Structure| 16847-90-8

Structure of 16847-90-8

Chemical Structure| 16847-90-8

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Product Details of [ 16847-90-8 ]

CAS No. :16847-90-8
Formula : C24H26ClO3P
M.W : 428.89
SMILES Code : O=C(C([P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)OCC)OCC.[Cl-]
MDL No. :MFCD00159378

Safety of [ 16847-90-8 ]

Application In Synthesis of [ 16847-90-8 ]

* 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 [ 16847-90-8 ]

[ 16847-90-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 635712-99-1 ]
  • [ 16847-90-8 ]
  • ethyl (2Z)-3-[6-(benzyloxy)pyridin-3-yl]-2-ethoxyacrylate [ No CAS ]
  • [ 791-28-6 ]
YieldReaction ConditionsOperation in experiment
With N,N,N1,N1-tetramethylguanidine; ammonium chloride; In chloroform; Preparation d-5 Ethyl (2Z)-3-[6-(benzyloxy)pyridin-3-yl]-2-ethoxyacrylate To a solution of <strong>[635712-99-1]6-(benzyloxy)nicotinaldehyde</strong> (1.0 eq., 33.1 mmol, 7.05 g) and (1,2-diethoxy-2-oxoethyl)(triphenyl)phosphonium chloride (2.0 eq., 66.2 mmol, 28.4 g) in chloroform (165 mL, 0.2 M) was added tetramethylguanidine (3.0 eq., 99.3 mmol, 11.4 g). The flask was capped with a hollow glass stopper and stirred at room temperature overnight. TLC analysis after approximately 18 hours indicated the presence of a small amount of unreacted starting material. The reaction mixture was heated to reflux and TLC reanalyzed after 2 hours. The reaction was quenched with saturated ammonium chloride. The layers were separated and the organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacua. A large amount of triphenylphosphine oxide precipitated. The residue was triturated with ether and filtered. Washed filter cake with ether and concentrated combined filtrates in vacuo to afford a pale yellow solid which was dissolved in a minimal amount of DCM and loaded onto Biotage Sp4 65i and eluted over a gradient of 10-100% hexanes to ethyl acetate. Obtained 12.3 g of a clear, colorless oil (37.6 mmol, quant.). LRMS: 328 (M+H)+. 1H NMR (DMSO-d6, 400 MHz): delta 8.33 (1 H, s) 7.92 (1 H, d, J=8.0 Hz) 7.31-7.43 (5 H, m) 6.76 (1 H, d, J=8.1 Hz) 6.60 (1 H, s) 5.37 (2 H, s) 4.23 (2 H, q, J=7.1 Hz) 3.90-3.99 (2 H, m) 1,34 (6 H, dt, J=15.8, 7.0 Hz).
  • 2
  • [ 635712-99-1 ]
  • [ 16847-90-8 ]
  • ethyl (2Z)-3-[6-(benzyloxy)pyridin-3-yl]-2-ethoxyacrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With N,N,N',N'-tetramethylguanidine; In chloroform; at 20℃; for 20h;Heating / reflux; To a solution of 6-(benzyloxy) nicotinaldehyde (1. 0 eq., 33. 1 mmol, 7. 05 G) and (1, 2-diethoxy-2-oxoethyl) (triphenyl) phosphonium chloride (2. 0 eq., 66. 2 mmol, 28. 4 g) in chloroform (165 mL, 0. 2 M) was added tetramethylguanidine (3. 0 eq., 99. 3 mmol, 11. 4 G). The flask was capped with a hollow glass stopper and stirred at room temperature overnight. TLC analysis after approximately 18 hours indicated the presence of a small amount of unreacted starting material. The reaction mixture was heated to reflux and TLC reanalyzed after 2 hours. The reaction was quenched with saturated ammonium chloride. The layers were separated and the organic layer was washed with brine, dried over magnesium sulfate and concentrated IN VACUO. A large amount of triphenylphosphine oxide precipitated. The residue was triturated with ether and filtered. Washed filter cake with ether and concentrated combined filtrates in vacuo to afford a pale yellow solid which was dissolved in a minimal amount of DCM and loaded onto Biotage SP4 65i and ELUTED over a gradient of 10-100 % hexanes to ethyl acetate. Obtained 12. 3 G of a clear, colorless oil (37. 6 MMOL, quant.). LRMS : 328 (M+H) *. 'H NMR (DMSO-D6, 400 MHz) ; 8. 33 (1 H, s) 7. 92 (1 H, d, J=8. 0 Hz) 7. 31-7. 43 (5 H, m) 6. 76 (1 H, d, J=8. 1 Hz) 6. 60 (1 H, s) 5. 37 (2 H, s) 4. 23 (2 H, Q, J=7. 1 Hz) 3. 90-3. 99 (2 H, m) 1. 34 (6 H, dt, J=15. 8, 7. 0 HZ)
 

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