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Chemical Structure| 209747-04-6

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Product Details of [ 209747-04-6 ]

CAS No. :209747-04-6
Formula : C16H16O2
M.W : 240.30
SMILES Code : OC1CC(C2=CC=CC=C2)C3=C(O1)C=CC(C)=C3
MDL No. :MFCD23104241

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* 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 [ 209747-04-6 ]

[ 209747-04-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 40546-94-9 ]
  • [ 108-18-9 ]
  • [ 851789-43-0 ]
  • [ 124937-51-5 ]
  • [ 209747-04-6 ]
YieldReaction ConditionsOperation in experiment
Following procedure similar to that described in patent US-A-5 922 914, a solution of 100 mg (0.42 MMOL) of (IIA), having [a] D20 =-2. 8 (CHC13, c = 1.44) and prepared according to the preceding Example 2, in anhydrous toluene (3 ML), was placed in a 100-MT two-necked flask that had been flamed beforehand. A solution of 1 M. DIBAL in toluene (440 ul, 0.44 MMOL) was added dropwise to this solution, under N2 and AT-25GC. The reaction was monitored by GC-MS and was stopped with 3 ml of ethyl acetate AT-25°C after 5 h, when GC-MS showed there was formation of 6-methyl-4-phenyl-chroman-2-ol at 89percent, together with unreacted starting product (7percent) and a product of further reduction [3- phenyl-3 (2'hydroxy, 5 METHYL) PHENYL-PROPAN-1-OL] (4percent). 3 ml of a 23percent citric acid solution was added. The solution was stirred at room temperature over night. The organic phase was separated and washed with H20, dried over NA2SO4, filtered and the solvent was removed by evaporation at reduced pressure. The raw product thus obtained was placed in a glass cylinder in an autoclave. CH30H (5 ML), Pd/C 5percent (20 mg), (PRI) 2NH (147 LUI, 1.05 MMOL) and H2 were added at 5 atmospheres. The reaction was continued for 12 h at 48°C. The temperature was brought back to room temperature and the autoclave was depressurized by eliminating the gas. After filtration of the catalyst on celite, a GC-MS analysis was carried out, which showed 6-methyl-4-phenyl-chroman-2-ol (2percent), (IIA) 5percent, [3-PHENYL-3 (2 HYDROXY, 5 METHYL) PHENYL-PROPAN-1-OL] (16percent), and (S)- TOLTERODINE (77percent). The raw product was purified by flash chromatography on SI02 (hexane: EtOAc (7: 3) /Et3N 98: 2) to give a colourless oil (100 mg; 73percent); [a] D20 =-23 (c = 1.5 ; CH30H).
 

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