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Chemical Structure| 3285-40-3 Chemical Structure| 3285-40-3

Structure of 3285-40-3

Chemical Structure| 3285-40-3

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Product Details of [ 3285-40-3 ]

CAS No. :3285-40-3
Formula : C19H19NO3
M.W : 309.36
SMILES Code : O=C(OCC1=CC=CC=C1)CC2=C(C)NC3=C2C=C(OC)C=C3

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Application In Synthesis of [ 3285-40-3 ]

* 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 [ 3285-40-3 ]

[ 3285-40-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 2882-15-7 ]
  • [ 501-53-1 ]
  • [ 3285-40-3 ]
  • 2
  • [ 2882-15-7 ]
  • [ 100-51-6 ]
  • [ 3285-40-3 ]
YieldReaction ConditionsOperation in experiment
84% 5-Methoxy-2-methyl-1H-indole-3-acetic acid (4.00 g, 18.26 mmol) and BOP-Cl (4.65 g, 18.26 mmol) were suspended in dichloromethane (1 mL) and NEt3 (5.0 mL, 35.90 mmol) was slowly added and the mixture stirred for 10 min. Benzyl alcohol (1.9 mL, 18.26 mmol) was added and the mixture stirred for 12 h. Dichloromethane (200 mL) was added and the reaction mixture was washed with water (2 × 200 mL) and brine solution (100 mL). The organic layer was concentrated and purified by column chromatography with a mixture of hexanes (80-100 C) and ethyl acetate (2:1) for elution. The solvent was removed under reduced pressure to yield the corresponding ester as yellow solid. Yield: 4.74 g (84%); elemental Anal. Calcd for C19H19NO3: C, 73.77; H, 6.19. Found: C, 73.13; H, 6.19; mp: 55-56 C; ESI MS (+) (CH3OH/CHCl3): m/z: 326.1 (100%, [M+OH]+); 1H NMR (CDCl3, ppm): 7.75 (s, br, 1H, NHindole), 7.29-7.23 (vbr, 5H, CHphenyl, together with solvent residual peak), 7.06 (d, 3JHH = 8 Hz, 1H, CHindole), 6.96 (d, 4JHH = 2 Hz, 1H, CHindole), 6.75 (dd, 3JHH = 8 Hz, 4JHH = 2 Hz, 1H, CHindole), 5.10 (s, 2H, CH2 benzyl), 3.76 (s, 3H, OCH3), 3.69 (s, 2H, CH2), 2.29 (s, 3H, CH3); 13C{1H} NMR (CDCl3, ppm): 172.0 (COO), 154.0 (CindoleO), 136.0 (Caromat), 133.7 (Caromat), 130.1 (Caromat), 128.8 (Caromat), 128.5 (CHphenyl), 128.1 (CaromatH), 128.0 (CHphenyl), 111.0 (CaromatH), 111.0 (CaromatH), 104.1 (Caromat), 100.2 (CaromatH), 66.5 (CH2 benzyl), 55.8 (OCH3), 30.5 (CH2), 11.7 (CH3); IR (selected, KBr, cm-1): = 3400 (s, nu(N-H)), 3033 (w), 2938 (w), 1729 (s, nu(CO)).
 

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