Trimethylsilyl Trifluoromethanesulfonate

Used Chemicals

• Trimethylsilyl Triflate [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 Reference

• 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.

References

• 1)An Extremely Fast and Efficient Acylation Reaction of Alcohols with Acid Anhydrides in the Presence of Trimethylsilyl Trifluoromethanesulfonate as Catalyst
  • P. A. Procopiou, S. P. D. Baugh, S. S. Flack, G. G. A. Inglis, Chem. Commun. 1996, 2625.
• 2)An Extremely Powerful Acylation Reaction of Alcohols with Acid Anhydrides Catalyzed by Trimethylsilyl Trifluoromethanesulfonate
  • P. A. Procopiou, S. P. D. Baugh, S. S. Flack, G. G. A. Inglis, J. Org. Chem., 1998, 63, 2342.
• 3)Protection for the Hydroxyl Group, Including 1,2- and 1,3-Diols
  • P. G. M. Wuts, in Greene’s Protective Groups in Organic Synthesis, 5th ed., ed. by P. G. M. Wuts, John Wiley & Sons, Inc., Hoboken, New Jersey, 2014, Chap. 2, 17.

Reference

• Protection for the Hydroxyl Group, Including 1,2- and 1,3-Diols
  • P. G. M. Wuts, in Greene’s Protective Groups in Organic Synthesis, 5th ed., ed. by P. G. M. Wuts, John Wiley & Sons, Inc., Hoboken, New Jersey, 2014, Chap. 2, 17.

References

• H. H. Hergott, G. Simchen, Liebigs Ann. Chem. 1980, 1718.
• G. Simchen, W. Kober, Synthesis 1976, 259.
• H. Emde, A. Gotz, K. Hofmann, G. Simchen, Liebigs Ann. Chem. 1981, 1643.
• S. Hashimoto, M. Hayashi, R. Noyori, Tetrahedron Lett. 1984, 25, 1379.
• S. Murata, M. Suzuki, R. Noyori, J. Am. Chem. Soc. 1980, 102, 3248.
• R. Noyori, S. Murata, M. Suzuki, Tetrahedron 1981, 37, 3899.