methyl 7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oate synthesis
- Product Name:methyl 7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oate
- CAS Number:14772-99-7
- Molecular formula:C25H40O5
- Molecular Weight:420.58
1448-36-8
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Yield:14772-99-7 98%
Reaction Conditions:
with Ag2CO3 on Celite in toluene;Reflux;Inert atmosphere;
Steps:
General procedure for the oxidation of the 3-hydroxyl group
To a solution of 1a (4.22 g, 10.0 mmol) in 200 mL toluene, freshly made Ag2CO3 on Celite4 (50% wt, 12.1 g, 22.0 mmol) was added in portions. Occasionally the suspension of Ag2CO3 on Celite had to be prerefluxed for 0.5 h to be activated and completely dehydrated. The suspension was refluxed and the water was removed by a Dean-Stark apparatus. The reaction was monitored by TLC until the starting material was consumed. The mixture was filtered to remove the solid, and the filtrate was concentrated in vacuo to provide a yellowish solid (2a, 4.1 g, 98% yield) with over 95% purity. Further purification was done by flash chromatography with eluent EA/Hex =1/2.
References:
Li, Qingjiang;Tochtrop, Gregory P. [Tetrahedron Letters,2011,vol. 52,# 32,p. 4137 - 4139] Location in patent:supporting information; experimental part
81-25-4
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$5.00/100mg
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