Trifluoroacetic acid → 1,1,5-Trimethylindan

HRID 2307936

Reaction equation

HRID 2307936 reaction equation
[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[CH:6][C:7]([CH3:11])=[CH:8][CH:9]=2)[C:4](=O)[CH2:3]1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+]>>[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[CH:6][C:7]([CH3:11])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 5945383,3,6-Trimethyl-1-indanone

Product 1

HCID 5894471,1,5-TrimethylindanYield 92%

Procedure

A solution of 3,3,6-trimethylindan-1-one (2.62 g, 15 mmol) in trifluoroacetic acid (12 mL, 150 mmol) was stirred at room temperature under nitrogen as triethylsilane (5.3 mL, 33 mmol) was added dropwise. The solution was stirred overnight. The reaction mixture was treated with saturated sodium bicarbonate, followed by extraction with ether. The combined ether layers were dried over anhydrous sodium sulfate and concentrated. MS analysis of the crude material showed the presence of triethylsilanol and hexaethyldisiloxane as the major by-products. The crude material was subjected to fractional distillation to afford 1,1,5-trimethylindane (307) (2.19 g, 92%) as a colorless liquid. Boiling pt 86-88° C. at 0.8 mmHg; 1H NMR (CDCl3) δ 1.24 (s, 6H), 1.90 (t, 2H), 2.31 (s, 3H), 2.85 (t, 2H), 7.02 (m, 3H).

Workup

  1. additionwas added dropwise
  2. extractionfollowed by extraction with ether
  3. dry with materialThe combined ether layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. distillationThe crude material was subjected to fractional distillation

Sources & evidence

ORD record
ord-c5376f92ce2341e097ddf4dcc46ed948
Source dataset
uspto-grants-2004_12
Patent number
US06833372B2

Linked notes

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