Реакция #62074

Уравнение реакции

Water

NaH

4-Bromo-thianthren-1-ol

Chloromethylmethylether

→

title compound

1-Bromo-4-methoxymethoxy-thianthrene

Растворители

DMF

Условия реакции

Обработка

1. 1
   workup.STIRRINGto stir at room temperature for 2 hours
2. 2
   Экстракцияwas then extracted
3. 3
   СушкаThe combined organic extracts were then dried (MgSO4)
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   Другоеto give a mild amber liquid
7. 7
   ДругоеThe crude residue was purified by flash chromatography (SiO2) (10:1, Hexanes/EtOAc)

Методика

To a cooled (0° C.) solution of 4-Bromo-thianthren-1-ol (1.0 g, 3.21 mmol) in DMF (12 ml) was added NaH (60% dispersed in mineral oil, 0.23 g, 9.63 mmol) portionwise over 30 minutes and stirred for a further 30 minutes at this temperature. Chloromethylmethylether (0.26 g, 3.241 mmol) was then added and the reaction allowed to stir at room temperature for 2 hours. Water was added to the mixture which was then extracted using EtOAc (3×50 ml). The combined organic extracts were then dried (MgSO4), filtered and concentrated in vacuo to give a mild amber liquid. The crude residue was purified by flash chromatography (SiO2) (10:1, Hexanes/EtOAc) to give the title compound as a mild amber oil that crystallised upon standing (1.11 g, 97%). m/z (LC-MS, ESP):, RT=5.55 min, (M++1)=355.

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