Chlorotrimethylsilane → HCID 21193748, compound

Temperature

-78 °C

Cuprous iodide (1.15 g, 6.05 mmol) in dry THF (10 ml) was treated at 0° C. with benzylmagnesium bromide (2 M in THF, 6.05 ml, 12.1 mmol) over a 3 minute period. The cuprate was stirred at 0° C. for 30 minutes and then cooled to -78° C. and then TMSCl (3.28 g, 30.2 mmol) in THF (5 ml) was added dropwise keeping the reaction temperature below -60° C. The mixture was stirred at below -60° C. for a further 10 minutes and then ethyl-3-(3-cyclopentyloxy-4-methoxyphenyl)-2-acetyl-prop-2-enoate (1 g, 3.01 mmol) in THF (5 ml) was added dropwise over 3 minutes. The mixture was stirred at below -60° C. for 45 minutes and then saturated NH4Cl (30 ml) and water (20 ml) were added. The mixture was allowed to warm to room temperature, the resultant precipitate was removed by filtration and the filtrate evaporated, the residue was dissolved in methylene chloride (200 ml), washed with water (30 ml), 1n HCl (50 ml) and water (30 ml), dried over Na2SO4 and the volatiles removed in vacuo. Flash chromatography (SiO2 ; EtOAc:hexane (1:9)) afforded ethyl-3-(3-cyclopentyloxy-4-methoxyphenyl)-2-acetyl-4-phenyl-butanoate (1.19 g), 92%) as a yellow oil.

1. customthe reaction temperature below -60° C
2. stirringThe mixture was stirred at below -60° C. for 45 minutes
3. temperatureto warm to room temperature
4. customthe resultant precipitate was removed by filtration
5. customthe filtrate evaporated
6. dissolutionthe residue was dissolved in methylene chloride (200 ml)
7. washwashed with water (30 ml), 1n HCl (50 ml) and water (30 ml)
8. dry with materialdried over Na2SO4
9. customthe volatiles removed in vacuo

ORD record

ord-b5d02f9653fd489a80a68a529bb1f283

Source dataset

uspto-grants-2000_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06103749