Reaction #1880960

Reaction equation

water

iodotrimethylsilane

5,6-dimethoxy-1-methylindane

iodotrimethylsilane

→

1-methylindane-5,6-diol

Yield 93.5%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Extractionthe product was extracted twice
2. 2
   WashThe combined extracts were washed with 100 ml of 40% sodium hydrogen sulfite solution, 100 ml of water and 50 ml of saturated sodium chloride solution
3. 3
   Dryingdried over sodium sulfate
4. 4
   Concentrationconcentrated on a rotary evaporator

Procedure

Over 90 min at room temperature, 27.5 ml (202 mmol) of iodotrimethylsilane were added dropwise with stirring to a solution of 19.4 g (101 mmol) of 5,6-dimethoxy-1-methylindane in 150 ml of acetonitrile. The mixture was stirred for a further 2.5 d at room temperature, in the course of which, after 48 h, again 10 ml (73.5 mmol) of iodotrimethylsilane were added. The reaction mixture was then poured into 500 ml of water and the product was extracted twice, each time with 200 ml of ether. The combined extracts were washed with 100 ml of 40% sodium hydrogen sulfite solution, 100 ml of water and 50 ml of saturated sodium chloride solution, dried over sodium sulfate and concentrated on a rotary evaporator. After flash chromatography (pentane/ether, 2:1, Rf=0.28) on silica gel, 15.5 g (93%) of 1-methylindane-5,6-diol were obtained.

Source