Specifications
CLASS
Main-group Elements [Catalysis and Inorganic Chemistry]
SUBCLASS
Zinc [Catalysis and Inorganic Chemistry]
APPLICATION
Selective Deprotection of TES Groups using Zinc(II) Triflate
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.
Application
A Lewis Acid
Experimental procedure: to a mixture of 1,2-ethanedithiol (0.45 mL, 5.4 mmol) and zinc triflate (1.09 g, 3.0 mmol) in dichloromethane (5 mL) is added a solution of the ketone 1 (1.20 g, 1.68 mmol) in dichloromethane (5 mL) at 23 °C, and the reaction mixture is stirred for 3.5 h at 23 °C and for 2 h at reflux. Water (20 mL) is added and the resulting mixture is extracted with 1 : 1 diethyl ether-hexane. The extracts are washed first with two 20 mL-portions of dilute hydrochloric acid, then with saturated aqueous sodium bicarbonate, dried (Na2SO4) and concentrated in vacuo to afford a straw-colored oil. Chromatography over silica gel using 100 : 3 dichloromethane-diethyl ether for elution affords 2 (1.10 g, 85%) as a yellow oil.
PUBCHEM SUBSTANCE ID
87577065.0
BEILSTEIN/REAXYS NUMBER
4028195.0
HAZARD STATEMENTS
H314 : Causes severe skin burns and eye damage.
PRECAUTIONARY STATEMENTS
P501 : Dispose of contents/ container to an approved waste disposal plant.
P260 : Do not breathe dusts or mists.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water/shower.
P301 + P330 + P331 : IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P363 : Wash contaminated clothing before reuse.
P304 + P340 + P310 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER/doctor.
P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor.
P405 : Store locked up.
*USAGE / SAFETY STATEMENT
For laboratory research and development purposes only.
QUALITY CERTIFICATION / COMPLIANCE
Fukaya factory is certified for GMP, ISO14001:2004 (JQA-EM5386) and IQ Net (JP-JQA-EM5386).
APPEARANCE
White to Almost white powder to crystal
MOLECULAR FORMULA
C2F6O6S2Zn
PURITY / ANALYSIS METHOD
>98.0%(T)