Hydrochloric Acid → (1r)-4-Hydroxy-1-methyl-1-(3-methylbutyl)naphthalen-2(1h)-one

A solution of Example 39D (3.10 g, 9.80 mmol) in 1,4-dioxane (25 mL) was treated with aqueous 1N hydrochloric acid solution (25 mL) and refluxed for 3 hours. The mixture was cooled to 25° C. and partitioned between ethyl acetate and water. The ethyl acetate layer was washed with water and brine, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was triturated in hot hexane and filtered. The precipitate was dried to give the title compound (2.10 g, 88%). 1H NMR (300 MHz, CDCl3): δ ppm 0.44 m, 0.5 H) 0.73 m, 3.5 H) 0.80 m, 3 H) 1.06 m, 1 H) 1.39 m, 1 H) 1.56 (s, 1.5 H) 1.59 (s, 1.5 H) 2.04 m, 1 H) 2.30 m, 1 H) 3.74 (s, 0.5 H) 3.75 (s, 0.5 H) 6.63 (s, 0.5 H) 7.46 m, 2 H) 7.66 m, 1 H) 8.08 m, 0.5 H) 8.20 m, 0.5 H).

1. temperaturerefluxed for 3 hours
2. custompartitioned between ethyl acetate and water
3. washThe ethyl acetate layer was washed with water and brine
4. dry with materialdried with sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was triturated in hot hexane
8. filtrationfiltered
9. customThe precipitate was dried

ORD-Eintrag

ord-69bf38aff1bd45f7b87e2ddb419355da

Quelldatensatz

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07378414B2