Réaction #62072

Équation de réaction

oxygen

t-BuLi

thianthrene

EtMgBr

→

title compound

Rendement 36.0%

Thianthren-1 -ol

Rendement 36.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Températurecooled
2. 2
   Autre(0° C.) reaction mixture which
3. 3
   Autrewas bubbled through the solution
4. 4
   AutreAfter two hours the reaction was quenched by dropwise addition of 1M NaOH (100 ml)
5. 5
   Lavagewashed with EtOAc (1×300 ml)
6. 6
   ExtractionThe mixture was then extracted with EtOAc (3×100 mL),dried (MgSO4),
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated in vacuo
9. 9
   Autreto give a mild amber slurry that
10. 10
    Autrewas purified by flash chromatography (SiO2) (10:1, Ethyl acetate/Hexanes)

Mode opératoire

To a cooled (−78° C.) solution of thianthrene (10 g, 46.23 mmol) in anhydrous THF (200 ml) was added t-BuLi (1.7M in pentane, 40.81 ml, 69.34 mmol), under a nitrogen atmosphere, over a period of 10 minutes and the resulting yellow solution was then allowed to warm to room temperature and stirred vigorously for a further 16 hours. EtMgBr (3M in THF, 23 ml, 69.34 mmol) was then added in a dropwise fashion to the cooled (0° C.) reaction mixture which was then stirred for a further 45 minutes before oxygen was bubbled through the solution. After two hours the reaction was quenched by dropwise addition of 1M NaOH (100 ml) and washed with EtOAc (1×300 ml) before being acidified to pH4 with aqueous 1M HCl. The mixture was then extracted with EtOAc (3×100 mL),dried (MgSO4), filtered and concentrated in vacuo to give a mild amber slurry that was purified by flash chromatography (SiO2) (10:1, Ethyl acetate/Hexanes), to give the title compound (3.82 g, 36%) as a yellow solid. m/z (LC-MS, ESP):, RT=4.62 min, (M++1)=231

Source