ChemicalBook CAS DataBase List 4-(TRIMETHYLSILYLETHYNYL)BENZYL ALCOHOL

4-(TRIMETHYLSILYLETHYNYL)BENZYL ALCOHOL synthesis

12synthesis methods

Product Name:4-(TRIMETHYLSILYLETHYNYL)BENZYL ALCOHOL
CAS Number:275386-60-2
Molecular formula:C12H16OSi
Molecular Weight:204.34

77123-57-0 Synthesis

77123-57-0
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$15.00/1g

275386-60-2
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$10.00/100mg

Yield: 94%

Reaction Conditions:

Stage #1:4-[(trimethylsilyl)ethynyl]bezaldehyde with sodium tetrahydroborate in ethanol at 20;
Stage #2: with water;ammonium chloride in ethanol

Steps:

4.B
Part B: Synthesis of 4- [(TrimethylsilvDethynyl-phenyll methanolTo a stirred solution of 4-[(trimethylsilyl)ethynyl]benzaldehyde (0.50 g, 2.47 mmol) in dry ethanol (10 ml) was added sodium borohydride (0.32 g, 8.50 mmol). The reduction was almost instantaneous at room temperature. The reaction mixture was carefully quenched with half-saturated aqueous ammonium chloride solution (30 ml) and extracted with dichloromethane (2 x 20 ml). The combined organic layers were washed with saturated brine (2 x 15 ml), dried over MgSO₄, filtered and concentrated under reduced pressure to yield 4-[(trimethylsilyl)ethynyl-phenyl]methanol (0.47 g, 2.32 mmol, 94%). The material was used in the next step without any further purification.¹H-NMR (CDCl₃, 200 MHz): δ[ppm] = 0.25 (s, 9H), 1.65 (t, IH, J = 5.9 Hz), 4.69 (d, 2H₅ J = 5.8 Hz), 7.29 (d, 2H, J = 8.3 Hz), 7.46 (d, 2H, J = 8.3 Hz)

References:

COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION WO2008/31157, 2008, A1 Location in patent:Page/Page column 64-65