Hydrochloric Acid → HCID 11094617, compound

To a stirred solution of lithium diisopropylamide mono (tetrahydrofuran) (100 ml, 150 mM, 1.5M solution) in dry tetrahydrofuran (100 ml) under an atmosphere of nitrogen and at -78° C. was added dropwise 3-ethoxy-2-cyclohexen-1-one (21.0 g, 150 mM) dissolved in tetrahydrofuran (70 ml) over a period of 15 min. After an additional 45 min, methyl iodide (21.29 g, 150 mM) dissolved in dry tetrahydrofuran (10 ml) was added dropwise over a period of 5 min. After a further 15 min the cooling bath was removed and the whole stirred at room temperature for 1 h. Water was then added and the enol ether intermediate recovered into ether, washed (brine), dried (Na2SO4) and evaporated to dryness. The oil thus obtained was dissolved in ethanol (100 ml) and 5N hydrochloric acid (228 ml) added. The whole was stirred at room temperature for 45 min. Water (800 ml) was added, the aqueous phase made basic to pH 8-9 (NaOH) and extracted with ethyl acetate. The aqueous phase was re-acidified (HCl) and the product extracted into ethyl acetate. The organic phase was washed with brine, dried (Na2SO4) and evaporated to give the title compound (D11) (17.6 g) (92%) as an oil. Product could be used directly in the preparation of intermediate D13 without further purification.

1. additionwas added dropwise over a period of 5 min
2. customAfter a further 15 min the cooling bath was removed
3. additionWater was then added
4. customthe enol ether intermediate recovered into ether
5. washwashed (brine)
6. dry with materialdried (Na2SO4)
7. customevaporated to dryness
8. customThe oil thus obtained
9. stirringThe whole was stirred at room temperature for 45 min
10. extractionextracted with ethyl acetate
11. extractionthe product extracted into ethyl acetate
12. washThe organic phase was washed with brine
13. dry with materialdried (Na2SO4)
14. customevaporated

ORD record

ord-7b657d9797ac495e956bb1e160bc1c9b

Source dataset

uspto-grants-1992_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05079246