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Chemical Structure| 1392846-44-4 Chemical Structure| 1392846-44-4

Structure of 1392846-44-4

Chemical Structure| 1392846-44-4

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Product Details of [ 1392846-44-4 ]

CAS No. :1392846-44-4
Formula : C12H16BrNO3
M.W : 302.16
SMILES Code : O=C(OC(C)(C)C)NCC1=CC(Br)=CC=C1O

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Application In Synthesis of [ 1392846-44-4 ]

* 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 [ 1392846-44-4 ]

[ 1392846-44-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 675149-75-4 ]
  • [ 1392846-44-4 ]
  • tert-butyl (5-bromo-2-(oxazol-4-ylmethoxy)benzyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% Compound 103 (0.556 g, 1.8 mmol) and Cs2CO3(1.25 g, 3.8 mmol) were diluted at r.t. in anhydrous DMF (9.0 mL). After being stirred for 30 min under a nitrogen stream, <strong>[675149-75-4]4-(chloromethyl)oxazole hydrochloride</strong> (0.252 g, 2.2 mmol) was added to the mixture. The reaction vessel was sealed under nitrogen and left to stir at r.t. for 18 h. After 18 h of continuous stirring, a second portion of <strong>[675149-75-4]4-(chloromethyl)oxazole hydrochloride</strong> (0.055 g, 0.47 mmol) was added to the mixture, and stirring was continued for an additional 18 h. The mixture was poured into 100 mL of sat. aq. NaHCO3 solution and extracted with four 100 mL portions of EtOAc. The organic fractions were combined and washed once with sat. aq. NaCl, dried over anhydrous sodium sulfate, and concentrated to yield an oily residue. The residue was purified by flash column chromatography, eluting with a gradient of 5% EtOAc in hexanes to 55% EtOAc in hexanes to yield 115 as a yellow semi-solid (0.401 g, 57 %): mp 94.1-95.7 C;1H-NMR (500 MHz, CDCl3) δ 7.91 (s, 2 H), 7.75 (s, 2 H), 7.39 (d, J = 2.5 Hz, 2 H), 7.34 (dd, J = 8.7, 2.5 Hz, 2 H), 6.84 (d, J = 8.7 Hz, 2H), 5.16 (s, 2 H), 5.05 (d, J = 1.0 Hz, 4 H), 4.29 (d, J = 6.2 Hz, 3 H), 2.96 (s, 1 H), 2.88 (s, 1 H), 1.44 (s, 17 H); 13C NMR (126 MHz, CDCl3) δ 162.5, 155.8, 155.2, 151.5, 136.8, 136.3, 132.1, 131.2, 130.1, 113.6, 79.5, 62.9, 39.9, 36.5, 31.4, 28.4; LC-TOF ESI m/z 384/386 (MH+).
 

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