Trifluoroacetic acid → 1,1,5-Trimethylindan

HRID 2307936

反応式

HRID 2307936 の反応式
[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

参加物

5

反応物 4

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

生成物 1

HCID 5894471,1,5-Trimethylindan収率 92%

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c5376f92ce2341e097ddf4dcc46ed948
出典データセット
uspto-grants-2004_12
特許番号
US06833372B2

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