Specifications
CLASS
Aryne Precursors, Heteroaryne Precursors
SUBCLASS
Benzyne Precursors
APPLICATION
Three-Component coupling of benzyne, DMF, and active methylene compounds to produce coumarins
Typical procedure (Entry 1): A Schlenk tube is charged with KF (46.5 mg). The tube is evacuated at room temperature for 1 h before addition of DMF (4 mL), diethyl malonate (32 mg), and 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (119.3 mg) under an argon atmosphere. The resulting mixture is stirred at 80 ºC for 5 h. The mixture is diluted with ethyl acetate and the organic solution is washed three times with brine. The organic layer is dried over MgSO4 and the solvent is removed in vacuo. The residue is purified by silica-gel column chromatography to give ethyl 2-oxo-2H-chromene-3-carboxylate as a pale yellow solid (34.2 mg, 79 % yield based on diethyl malonate).
PUBCHEM SUBSTANCE ID
87559751.0
BEILSTEIN/REAXYS NUMBER
5574211.0
HAZARD STATEMENTS
H314 : Causes severe skin burns and eye damage.
H290 : May be corrosive to metals.
PRECAUTIONARY STATEMENTS
P501 : Dispose of contents/ container to an approved waste disposal plant.
P234 : Keep only in original container.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P390 : Absorb spillage to prevent material damage.
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.
P406 : Store in corrosive resistant container with a resistant inner liner.
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
Colorless to Light yellow clear liquid
MOLECULAR FORMULA
C10H13F3O3SSi
PURITY / ANALYSIS METHOD
>95.0%(GC)
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