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TCI Practical Example: Synthesis of a Silyl Enol Ether Using Trimethylsilyl Triflate

We are proud to present the synthesis of the silyl enol ether from α-tetralone using trimethylsilyl triflate.

Used Chemicals

• Trimethylsilyl Triflate (= TMSOTf) [T0871]
• α-Tetralone [T0134]
• Triethylamine (= Et₃N) [T0424]
• Dichloromethane

Procedure

A solution of triethylamine (0.95 mL, 6.8 mmol) and α-tetralone (0.5 g, 3.4 mmol) in dichloromethane (14 mL) was cooled with an ice bath and trimethylsilyl triflate (0.74 mL, 4.1 mmol) was added. After stirring at room temperature for 6 hours, water (20 mL) was added to the reaction solution and the two layers were separated. The aqueous layer was extracted with dichloromethane (10 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (hexane:ethyl acetate = 9:1) to afford (3,4-dihydro-1-naphthyloxy)trimethylsilane (602 mg, 81% yield) as a white solid.

Experimenter's Comments

The reaction solution was monitored by UPLC.

Analytical Data

¹H NMR (400 MHz, DMSO-d₆); δ 7.42 (d, J = 7.2 Hz, 1H), 7.20-7.14 (m, 3H), 5.23 (t, J = 4.6 Hz, 1H), 2.79-2.76 (m, 2H), 2.36-2.31 (m, 2H), 0.29 (s, 9H).

Other References

• Synthesis of novel mast cell-stabilising and anti-allergic 1,2,3,4-tetrahydro-1-naphthalenols and related compounds
  • J. W. Barlow, A. P. McHugh, O. Woods, J. Walsh, Eur. J. Med. Chem. 2011, 46, 1545.