| Identification | Back Directory | [Name]
Phenol, 2-[(trimethylsilyl)ethynyl]- | [CAS]
81787-62-4 | [Synonyms]
2-((Trimethylsilyl)ethynyl)phenol
o-((trimethylsilyl)ethynyl)phenol
Phenol, 2-[(trimethylsilyl)ethynyl]-
2-[2-(Trimethylsilyl)ethynyl]-phenol
Phenol, 2-[2-(trimethylsilyl)ethynyl]- | [Molecular Formula]
C11H14OSi | [MDL Number]
MFCD22418462 | [MOL File]
81787-62-4.mol | [Molecular Weight]
190.31 |
| Hazard Information | Back Directory | [Synthesis]
General method: 2-iodophenol (1 mmol) was dissolved in a solvent mixture of anhydrous THF and Et3N (2:1 v/v, 10 mL) under argon protection. Pd(PPh3)2Cl2 (0.025 mmol) and CuI (0.05 mmol) were subsequently added. Trimethylsilylacetylene (1.3 mmol) was slowly added dropwise at room temperature and the reaction mixture was stirred for 4 hours (the progress of the reaction was monitored by TLC). Upon completion of the reaction, the solvent was removed by concentration under reduced pressure and the residue was purified by column chromatography on silica gel (100-200 mesh), using a mixture of diethyl ether and petroleum ether solvent (4-10%) as eluent, to afford pure 2-((trimethylsilyl)alkynyl)phenol in good yields (see Table 1). | [References]
[1] Journal of the American Chemical Society, 2005, vol. 127, # 1, p. 201 - 209
[2] Journal of Organic Chemistry, 2002, vol. 67, # 15, p. 5138 - 5141
[3] Angewandte Chemie - International Edition, 2012, vol. 51, # 24, p. 5857 - 5861
[4] Journal of Organic Chemistry, 1996, vol. 61, # 26, p. 9280 - 9288
[5] Journal of Organic Chemistry, 2004, vol. 69, # 6, p. 2084 - 2093 |
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