Reaktion #2307368

Reaktionsgleichung

[(4-iodoimidazolyl)sulfonyl]dimethylamine

ethylmagnesium bromide

ammonium chloride

6-methoxy-7-methylchroman-4-one

6-Methoxy-7-methyl-chroman-4-one

→

subject compound

Ausbeute 56.1%

{[4-(4-Hydroxy-6-methoxy-7-methylchroman-4-yl)imidazolyl]sulfonyl}dimethylamine

Ausbeute 56.1%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONUpon completion of addition
2. 2
   workup.STIRRINGthe reaction mixture was stirred for an additional 18 hours
3. 3
   Extraktionextracted with three 100 mL portions of methylene chloride
4. 4
   WaschenThe combined extracts were washed with one 50 mL portion of water
5. 5
   Trocknendried with sodium sulfate
6. 6
   FiltrationThe mixture was filtered
7. 7
   Einengenthe filtrate was concentrated under reduced pressure to a residue
8. 8
   SonstigeThe residue was purified by column chromatography on Grade II basic alumina (3% water)
9. 9
   workup.ADDITIONa 99:1 mixture of methylene chloride and methanol
10. 10
    Einengenconcentrated under reduced pressure

Vorschrift

A solution of 4.6 grams (0.016 mole) of [(4-iodoimidazolyl)sulfonyl]dimethylamine (commercially available) in 10 mL of dry methylene chloride was stirred and 5.7 mL (0.018 mole) of ethylmagnesium bromide (3M in diethyl ether) was added. Upon completion of addition, the reaction mixture was stirred during a 2.5 hour period. After this time, 3.0 grams (0.016 mole) of 6-methoxy-7-methylchroman-4-one (ii) (prepared in Step C of Example 5) was added, and the reaction mixture was stirred for an additional 18 hours. After this time, the reaction mixture was poured into 100 mL of an aqueous solution of ammonium chloride and extracted with three 100 mL portions of methylene chloride. The combined extracts were washed with one 50 mL portion of water, and dried with sodium sulfate. The mixture was filtered and the filtrate was concentrated under reduced pressure to a residue. The residue was purified by column chromatography on Grade II basic alumina (3% water) using a 99:1 mixture of methylene chloride and methanol, respectively, as an eluant. The appropriate fractions of eluate were combined and concentrated under reduced pressure, yielding 3.3 grams of the subject compound. The NMR spectrum was consistent with the proposed structure.

Quelle