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Chemical Structure| 99758-42-6 Chemical Structure| 99758-42-6

Structure of 99758-42-6

Chemical Structure| 99758-42-6

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Product Details of [ 99758-42-6 ]

CAS No. :99758-42-6
Formula : C15H23NO3
M.W : 265.35
SMILES Code : O=[N+](C1=C(OC)C(C(C)(C)C)=CC(C(C)(C)C)=C1)[O-]

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Application In Synthesis of [ 99758-42-6 ]

* 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 [ 99758-42-6 ]

[ 99758-42-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 99758-42-6 ]
  • [ 893397-17-6 ]
YieldReaction ConditionsOperation in experiment
93% With ammonium formate;palladium 10% on activated carbon; In ethanol; at 20.0℃; for 1h; Scheme G2; [00333] Synthesis of GGl. Trifluoroacetic anhydride (1.35 mL, 9.52 mmol) was added dropwise to a solution of 2,4-di-fert-butylanisole (2.0 g, 9.08 mmol) and EPO <DP n="84"/>tetrabutylammonium nitrate (2.9 g, 9.52 mmol) in CH2Cl2 at OC under N2. The reaction was allowed to warm to rt. After 2h, the reaction was washed once with H2O, twice with 10% HCl (aq.), once with brine, and then dried over Na2SO4. The crude product mixture was cliromatographed on silica gel eluting with hexanes / EtOAc = 40 / 1. Isolated 1.96 g, 81% yield, of GGl as a yellow solid.[00334] Synthesis GG2. A reaction flask was charged, under N2, with GGl (133 mg, 0.50 mmol), 10% Pd/C (a couple of small. spatula scoops), EtOH (2.0 mL), and ammonium formate (158 mg, 2.50 mmol). After Ih at rt the reaction was filtered through a pad of Celite and washed through with EtOAc. The EtOAc solution was washed twice with H2O, once with brine, and then dried over Na2SO4. Isolated 110 mg, 93% yield, of GG2 as a white solid. The product was used directly in the next step without further purification.[00335] Synthesis of GG4. GG2 (110 mg, 0.47 mmol), 2-nitrobenzaldehyde (71 mg, 0.47 mmol), and p-TsOH (~ 10.0 mol%) were combined in THF (10 mL) over 3A molecular sieves. The reaction was heated at reflux for 4h. The sieves were removed by filtration and the reaction solution was concentrated to give imine GG3 as a yellow solid. GG3 was taken up in P(OEt)3 (1 mL) and heated at 100C for 18h. The reaction mixture was purified by silica gel chromatography eluting with hexanes / EtOAc = 20 / 1. Isolated 119 mg, 76% yield, of GG4 as a light yellow powder.[00336] Synthesis of Ligand G4. BBr3 (0.51 mL, 1.0 M in CH2Cl2) was added dropwise to a solution of GG4 (115 mg, 0.34 mmol) in CH2Cl2 (4 mL) at -78C under N2. The reaction was warmed slowly to rt and stirred overnight. The reaction was washed with sat. NaHCO3 (aq.), H2O, brine, and then dried over Na2SO4. Purified by silica gel chromatography eluting with hexanes / EtOAc = 10 / 1. Isolated 60 mg, 55% yield, of ligand G4 as a faint yellow solid. 1H NMR (300 MHz, C6D6) δ 1.32 (s, 9H, 'Bu), 1.68 (s, 9H, 'Bu), 6.93 (m, 1H), 7.10 (m, 2H), 7.42 (d, 1H), 7.52 (d, 1H), 7.57 (d, 1H), 7.65 (s, 1H), 12.70 (s, 1H, OH).
 

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