5,7-BIS-(BENZYLOXY)-2-(4-(BENZYLOXY)PHENYL)-3-HYDROXY-4H-CHROMEN-4-ONE synthesis

10synthesis methods

Product Name:5,7-BIS-(BENZYLOXY)-2-(4-(BENZYLOXY)PHENYL)-3-HYDROXY-4H-CHROMEN-4-ONE
CAS Number:23405-70-1
Molecular formula:C36H28O6
Molecular Weight:556.6

96333-59-4 Synthesis

5,7-BIS-(BENZYLOXY)-2-(4-(BENZYLOXY)PHENYL)-4H-CHROMEN-4-ONE

96333-59-4
18 suppliers
$85.00/5mg

5,7-BIS-(BENZYLOXY)-2-(4-(BENZYLOXY)PHENYL)-3-HYDROXY-4H-CHROMEN-4-ONE

23405-70-1
14 suppliers
$109.90/5mg

Yield:23405-70-1 78%

Reaction Conditions:

Stage #1: 5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-4H-chromen-4-onewith 3,3-dimethyldioxirane in dichloromethane;acetone at 0;
Stage #2: toluene-4-sulfonic acid in dichloromethane at 0; for 0.5 h;

Steps:

To a solution containing LOO g (1.85 mmol) of 3 in 30 mL of CH₂Cl₂ at 0⁰C was added 30 mL of a 0.9-0.11 M solution of DMDO in acetone. The reaction mixture was stirred at 0 ⁰C overnight under N₂. The solvent was concentrated under diminished pressure, and then the residue was redissolved in 50 mL OfCH₂Cl₂ and treated with catalytic pTsOH. The reaction mixture was stirred at 0 ⁰C for 30 min. The solvent was concentrated under diminished pressure and the residue was purified by flash chromatography on a silica gel column (25 x 4 cm). Elution with 1:1 hexanes-ethyl acetate gave 4 as a light brown solid: yield 0.63 g (78% based on consumed starting material) and 0.22 g of unreacted starting material; silica gel TLC R_f 0.28 (3:1 hexanes-ethyl acetate); ¹H NMR (DMSO-J₆) δ 5.19 (s, 2H), 5.25 (s, 2H), 6.69 (s, IH), 6.97 (br s, IH), 7.18 (d, 2H, J= 8.5 Hz), 7.30-7.44 (m, 11 H), 7.46-7.50 (m, 2H), 7.67 (d, 2H, J= 7.5 Hz), 8.14 (d, 2H, J= 8.5 Hz) and 9.15 (s, IH); ¹³C NMR (DMSO-^₆) δ 70.1, 70.5, 70.7, 94.6, 98.0, 102.2, 107.4, 115.6, 127.2, 128.1, 128.5, 128.6, 128.7, 128.87, 128.92, 129.16, 129.23, 129.4, 136.8, 137.4, 137.6, 138.8, 142.5, 158.7, 159.5, 159.8, 163.4 and 171.9; mass spectrum (FAB), m/z 551.1961 (M + H)⁺ (C₃₆H₂₉O₆ requires 557.1964).