Water → HCID 12084175, compound

HRID 1767440Notes

Reaction equation

HRID 1767440 reaction equation
I[Si](C)(C)C.C[O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][C:16]=1[O:17]C)[CH:13]([CH3:19])[CH2:12][CH2:11]2.O>C(#N)C>[CH3:19][CH:13]1[C:14]2[C:10](=[CH:9][C:8]([OH:7])=[C:16]([OH:17])[CH:15]=2)[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 85247Trimethylsilyl iodide2×HCID 14024789HCID 14024789, compound

Product 1

HCID 12084175HCID 12084175, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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.

Workup

  1. extractionthe product was extracted twice
  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. dry with materialdried over sodium sulfate
  4. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-8740e8392c2342bb81798520d780bec1
Source dataset
uspto-grants-2007_06
Patent number
US07235519B2

Reaction notes

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