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20th August 2013 @ 10:35

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Reaction information

*#Reaction file
reactionscheme_37.cdx
*Reaction file type CDX
*Procedure A 50 mL Schlenk flask containing lithocholic acid (1.88 g, 4.99 mmol) was evacuated and refilled with argon; a solution of isopropylmagnesium bromide  2 M in Et2O (6.25 mL, 12.50 mmol, 2.50 eq.) was then added, yielding a white suspension that was cooled to 0 °C. To a small Schlenk tube containing bis[π-cyclopentadienyl]titanium dichloride (12 mg, 0.05 mmol, 1 mol%), previously evacuated and refilled with argon, was added a solution of isopropylmagnesium bromide  2 M in Et2O (3.75 mL, 7.50 mmol, 1.50 eq.); the resulting blue solution was cooled at 0 °C for 5 minutes and then added to the flask containing the lithocholic acid suspension. The reaction mixture was let warming to r.t. and stirred for 5 hours. Then the excess Grignard reagent was quenched with HCl 2 N; after most of the solvent had been removed in a rotating evaporator, the mixture was diluted with DCM and washed with water and brine. Drying over MgSO4 and evaporation of the solvent yielded the pure title compound (white solid; 239 mg, 0.66 mmol, yield 13 %).
*Yield (%) 13 %
*Type of Yield Isolated pure product
Reference(s)
PhD Thesis - 16Sep2010_final p18.pdf
 
PhD Thesis - 16Sep2010_final p126-127.pdf
Further information Compound 37: (R)-4-((3R,10S,13R,17R)-Hexadecahydro-3-hydroxy-10,13-dimethyl-1H-cyclopenta[α]phenanthren-17-yl)pentanal

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Attached Files
reactionscheme_37.cdx
PhD Thesis - 16Sep2010_final p18.pdf
PhD Thesis - 16Sep2010_final p126-127.pdf