Deoxy Artemisinin synthesis
- Product Name:Deoxy Artemisinin
- CAS Number:72826-63-2
- Molecular formula:C15H22O4
- Molecular Weight:266.33
71939-50-9
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Yield:-
Reaction Conditions:
with Thiomorpholin in ethanol for 20 h;Reflux;
Steps:
4.2.1 Attempted preparation from DHA by the Kotchetkov reaction
A solution of thiomorpholine (0.12mL, 1.2mmol) and dihydroartemisinin (DHA, 285.6mg, 1.01mmol) in ethanol (20mL) under nitrogen was heated under reflux for 20h. Half of the ethanol was then evaporated, and saturated aqueous ammonium chloride (5mL) was added followed by evaporation of remaining solvent under reduced pressure. The residue was triturated with dichloromethane, filtered and the filtrate was washed with brine (5mL). The organic layer was separated and dried (MgSO4), and after filtration, the solvent was evaporated under reduced pressure to leave a residue that was purified by column chromatography (25:75 ethyl acetate-hexane) to give deoxyartemisinin 6 (179mg, 67%). This was recrystallized from ethyl acetate-hexane to give 6 as colourless rectangular plates, m. p. 114-115.8°C, δH 0.95-0.97 (3H, d, J=5.0Hz, 6 Me), 1.20-1.23 (3H, d, J=2.4Hz, 9 Me), 1.27-1.29 (2H, m), 1.54-1.65 (7H, m), 1.76-2.06 (5H, m), 3.18-3.24 (1H, m), 5.70 (1H, s, H-12); m/z (%) 151.2 (13) 164.2 (30), 193.2 (16), 203.2 (34), 222.3 (21), 267.2 (100); HRMS (ESI) calcd. 267.1596 [M++1], found 267.1605. This sample was identical with that of deoxyartemisinin obtained by catalytic hydrogenation of artemisinin [4]. Repetition of the procedure with each of methanol, ammonium chloride (0.16g 3mmol) in 4:1 ethanol-water, and MgCl2 (0.1 equiv) in ethylene glycol at 40°C provided 2-deoxyartemisinin 6 as the only identifiable product in varying yields.
References:
Chan, Wing Chi;Wai Chan, Dennis Ho;Lee, Kin Wo;Tin, Wing Shan;Wong, Ho Ning;Haynes, Richard K. [Tetrahedron,2018,vol. 74,# 38,p. 5156 - 5171]
63968-64-9
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![Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-](/CAS/20210305/GIF/1000210-73-0.gif)
1000210-73-0
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72826-63-2
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1000210-73-0
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72826-63-2
79 suppliers
$25.00/1mg
1000210-73-0
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72826-63-2
79 suppliers
$25.00/1mg