Wogonin synthesis
- Product Name:Wogonin
- CAS Number:632-85-9
- Molecular formula:C16H12O5
- Molecular Weight:284.26
4431-41-8
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632-85-9
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Yield:632-85-9 36%
Reaction Conditions:
with 2,3-dicyano-5,6-dichloro-p-benzoquinone in 1,4-dioxane; for 16 h;Reflux;
Steps:
Wogonin (1)
A mixture of 7 (150 mg, 0.52 mmol), 1,4-dioxane (6 mL), and DDQ (357 mg, 1.57 mmol)was refluxed for 16 h, then filtered and the filtrate concentrated. The crude product waspurified by column chromatography (silica gel, EtOAc/hexane 2:1 acetone/CH2Cl2 1:1 acetone/CH2Cl2 2:1) to afford 1 as a dark yellow solid (54 mg, 36%) of m.p. 209 °C(ref. [1]: 201-202 °C); "max = 3078, 1717, 1655, 1612, 1570, 1445, 1377, 1358, 1304,1260, 1205, 1106, 1074, 1044, 892, 867, 859, 749, 660 cm-1; 1H NMR (300 MHz,CDCl3) 3.88 (s, 3H, CH3O), 6.04 (s, 1H, CH), 7.01 (s, 1H, CH), 7.47-7.60 (m, 3H),7.83-7.90 (m, 2H); MS (El), m/z (%): 284 (18) [M+], 269 (3), 230 (64), 228 (100), 202(42), 200 (65), 193 (8), 173 (4), 165 (4), 137 (13), 110 (18), 101 (12), 87 (27), 78 (11).
References:
Spoerlein-Guettler, Cornelia;Milius, Wolfgang;Obenauf, Johannes;Schobert, Rainer [Tetrahedron Letters,2016,vol. 57,# 14,p. 1560 - 1562] Location in patent:supporting information
3316-54-9
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632-85-9
301 suppliers
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3542-64-1
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632-85-9
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480-40-0
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$11.00/5g
632-85-9
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$29.00/10mg
642-71-7
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$6.00/100mg
632-85-9
301 suppliers
$29.00/10mg