Methyl iodide → HCID 22491048, compound

Temperature

-78 °C

To a solution of 1-(3-ethoxy-5,5-dimethyl-5,6-dihydro-naphthalen-2-yl)-ethanone (Compound A-25, 0.17 g, 0.68 mmol) in THF (33 mL) at −78° C. was added lithium diisopropylamide (1.5 M in cyclohexane, 0.55 mL 0.82 mmol). The cold bath was removed and the mixture was stirred for 2 h. The mixture was cooled to −78° C. again and methyl iodide (0.13 mL, 2.04 mmol) was added. The mixture was stirred at room temperature for 12 h then quenched with a saturated solution of NH4Cl and extracted with diethyl ether. The combined ethereal layers were washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (silica gel, 2% ethyl acetate in hexane) to give the title compound as a yellow oil.

1. customThe cold bath was removed
2. stirringThe mixture was stirred at room temperature for 12 h
3. customthen quenched with a saturated solution of NH4Cl
4. extractionextracted with diethyl ether
5. washThe combined ethereal layers were washed with water, brine
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude residue was purified by flash chromatography (silica gel, 2% ethyl acetate in hexane)

ORD record

ord-8d580488ada340a4b5bb9f4957c7ac4e

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06887896B1