Triethylsilane → 2,3-Dihydro-4,7-dimethoxy-1H-indene

HRID 389295Notes

Reaction equation

HRID 389295 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=O.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]2[C:8]=1[CH2:7][CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 6060124,7-dimethoxy-2,3-dihydro-1H-inden-1-one

Product 1

HCID 126541332,3-Dihydro-4,7-dimethoxy-1H-indene

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To the cooled and stirred suspension of 4,7-Dimethoxyindan-1-one (35 gm, 0.182 mole) in Triethyl silane (105.7 gm, 0.909 mole), added Trifluoroacetic acid (350 ml) at 10-15° C. The stirring was continued at room temperature for 2 hours and quenched into the water. It was extracted with Ethyl acetate. The Ethyl acetate layer was washed with Sodium bicarbonate solution, dried over Sodium sulphate and evaporated to give crude mass which was purified by column chouromatography using 5% Ethyl acetate in hexane (22.5 gm).

Workup

  1. temperatureTo the cooled
  2. customquenched into the water
  3. extractionIt was extracted with Ethyl acetate
  4. washThe Ethyl acetate layer was washed with Sodium bicarbonate solution
  5. dry with materialdried over Sodium sulphate
  6. customevaporated
  7. customto give crude mass which
  8. customwas purified by column chouromatography

Sources & evidence

ORD record
ord-b02e0f252d6443fe8f380246ef849ad5
Source dataset
uspto-grants-2013_02
Patent number
US08378118B2

Reaction notes

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