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Chemical Structure| 82065-19-8 Chemical Structure| 82065-19-8

Structure of 82065-19-8

Chemical Structure| 82065-19-8

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Product Details of [ 82065-19-8 ]

CAS No. :82065-19-8
Formula : C11H14O2
M.W : 178.23
SMILES Code : O[C@@H]1C[C@H](C2=CC=CC=C2)OCC1
MDL No. :MFCD17676159

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Application In Synthesis of [ 82065-19-8 ]

* 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.

  • Upstream synthesis route of [ 82065-19-8 ]

[ 82065-19-8 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 82065-19-8 ]
  • [ 147688-62-8 ]
YieldReaction ConditionsOperation in experiment
72%
Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.5 h;
Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at -78℃; for 3 h;
12 : 2-Phenyl-tetrahydro-pyran-4-one DMSO (615 mmol) was added dropwise into a solution of (COCl)2 (128 mmol) in CH2Cl2(100 mL) at -78 0C. The mixture was stirred at -78 0C for 15 min, then 2-phenyl-tetrahydro- pyran-4-ol (11) (84 mmol) in CH2Cl2 (50 mL) was added dropwise. The mixture was stirred at -78 0C for 30 min, then DIPEA (78 mL) was added dropwise at -78 0C and the resulting mixture was stirred for additional 3h. Water (100 mL) and CH2Cl2 (200 mL) were added, and the reaction mixture was stirred at room temperature for 15 min. The layers were separated and the organic fraction was washed with water x2, dried with Na2SO4 and concentrated in vacuo. The product was purified by flash chromatography on silica gel using 50percent ethyl acetate in petroleum ether as eluent to give the title compound. Yield = 72percent1H NMR (D6-DMSO): 2.44 (IH, d); 2.65 (IH, m); 2.66 (IH, t); 2.74 (IH, m); 3.85 (IH, dt); 4.44 (IH, m); 4.65 (IH, dd); 7.40-7.30 (m, 5H).
References: [1] Journal of the American Chemical Society, 1982, vol. 104, # 17, p. 4666 - 4671.
[2] Patent: WO2009/124882, 2009, A1, . Location in patent: Page/Page column 36.
[3] Chemische Berichte, 1955, vol. 88, p. 1053,1059.
[4] Bulletin de la Societe Chimique de France, 1954, p. 534.
 

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