ChemicalBook CAS DataBase List diphyllin

diphyllin synthesis

7synthesis methods

Product Name:diphyllin
CAS Number:22055-22-7
Molecular formula:C21H16O7
Molecular Weight:380.35

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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22055-22-7
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Yield: 88%

Reaction Conditions:

with piperidine in dichloromethane at 0 - 25; for 5 h;

Steps:

1-7 [Example 1-71 Synthesis of9-(benzo[dj [1,31 dioxol-5-yl)-4-hydroxy-6,7-dimethoxynaphtho[2,3-cj furan- 1 (3H)-one (diphyllin) [Scheme El
30.4 mgof9-(benzo[dj [1,31 dioxol-5-yl)-6,7-dimethoxy- 1 -oxo- 1 ,3-dihydronaphtho[2,3-cjfuran-4- yl t-butylcarbonate (0.063 mmol) was dissolved in 0.32 mL of dichloromethane (0.2 M) and 10.8 mg of piperidine (0.127 mmol) was added at 0 °C. After increasing reaction temperature to 25 °C, reaction was carried out for 5 hours. After terminating the reaction by adding 0.5 mL of 1 N hydrochloric acid aqueous solution, followed by extracting with EtOAc (3 x 1 mL), the organic layer was washed with brine (2 x 1 mL), dried with anhydrous Na2504, filtered and then concentrated. The remainder was purified by silica gel column chromatography to obtain 21.2 mg of the target compound9-(benzo[dj [1,31 dioxol-5-yl)-4-hydroxy-6,7-dimethoxynaphtho[2,3-cj furan- 1 (3H)-one (diphyllin) (0.056 mmol, 88%).1H NMR (400 MHz, DMSO-d6) 10.39 (s, 1H), 7.62 (s, 1H), 7.01 (d, 1H, J= 8.0 Hz), 6.95 (s, 1H), 6.68 (d, 1H, J= 1.6 Hz), 6.75 (dd, 1H, J= 1.6, 7.6 Hz), 6.11 (s, 2H), 5.36 (s, 2H), 3.94 (s, 3H), 3.65 (s, 3H).

References:

KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY;HAM, Jungyeob;KIM, Tae Jung;KWON, Hak Cheol;JEONG, Kyu Hyuk;SONG, Jungho;CHUNG, Bong Chul WO2014/119892, 2014, A1 Location in patent:Paragraph 114; 184; 185; 186; 187