Chlorotrimethylsilane

Used Chemicals

• Chlorotrimethylsilane (= TMSCl) [C0306]
• 3-Ethyl-3-pentanol [E0157]

Procedure

A mixture of 3-ethyl-3-pentanol (20.0 g, 172 mmol) and TMSCl (20.6 g, 189 mmol) was stirred at 70 °C for 4 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, and the volatile product was evaporated off under reduced pressure. The residue was distilled at atmospheric pressure (130 °C) to afford 3-chloro-3-ethylpentane (15.0 g, 65% yield) as a clear colorless liquid.

Experimenter’s Comments

The reaction was monitored by 1H NMR.

Analytical Data

3-Chloro-3-ethylpentane

¹H NMR (400 MHz, CDCl₃); δ 1.78 (q, J = 7.3 Hz, 6H), 0.96 (t, J = 7.3 Hz, 9H).

Lead Reference

• Direct halogenation of alcohols with halosilanes under catalyst- and organic solvent-free reaction conditions
  • N. Ajvazi, S. Stavber, Tetrahedron Lett. 2016, 57, 2430.

References

• 1)A Simple Method for the Esterification of Carboxylic Acids Using Chlorosilanes
  • R. Nakao, K. Oka, T. Fukumoto, Bull. Chem. Soc. Jpn. 1981, 54, 1267.
• 2)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.

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.

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

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.