Reaktion #63812

Reaktionsgleichung

t-butyllithium

3-methoxymethoxy-2-phenyl-7-azabenzothiophene

→

pale yellow needles

Ausbeute 84.0%

6-(1,1-dimethylethyl)-3-hydroxy-2-phenyl-7-azabenzo[b]thiophene

Ausbeute 84.0%

Lösungsmittel

hexane

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solution was quenched with methanol
2. 2
   Sonstigepartitioned between ether and water
3. 3
   WaschenThe aqueous layer was washed with two portions of ether
4. 4
   Waschenthe combined extracts were washed with brine
5. 5
   Sonstigedried
6. 6
   Einengenconcentrated to an oil
7. 7
   workup.DISSOLUTIONThe oil was dissolved in 10 mL methanol
8. 8
   workup.STIRRING10 mL of 2M HCl and stirred at room temperature for 24 hours
9. 9
   SonstigeThe solution was partitioned between ether and water
10. 10
    Trocknenthe ether layer dried
11. 11
    Einengenconcentrated
12. 12
    SonstigeRecrystallization from ether-hexane

Vorschrift

A solution of 2.72 g (10.0 mmol) of 3-methoxymethoxy-2-phenyl-7-azabenzothiophene in 20 mL of dry tetrahydrofuran was cooled to -78° C. To this was added 11 mL of a 1.0M solution of t-butyllithium in hexane and the solution was allowed to warm to room temperature. The solution was quenched with methanol and stirred in air for 60 minutes, then partitioned between ether and water. The aqueous layer was washed with two portions of ether and the combined extracts were washed with brine, dried, and concentrated to an oil. The oil was dissolved in 10 mL methanol and 10 mL of 2M HCl and stirred at room temperature for 24 hours. The solution was partitioned between ether and water and the ether layer dried and concentrated. Recrystallization from ether-hexane afforded 2.43 g (84%) of pale yellow needles, m.p. 181°-183° C.

Quelle