ChemicalBook CAS DataBase List 3-TRIMETHYLSILYLPROPYNAL

3-TRIMETHYLSILYLPROPYNAL synthesis

8synthesis methods

Product Name:3-TRIMETHYLSILYLPROPYNAL
CAS Number:2975-46-4
Molecular formula:C6H10OSi
Molecular Weight:126.23

1066-54-2
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$9.00/10g

2975-46-4
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$19.00/1g

Yield:2975-46-4 28%

Reaction Conditions:

with hydrogenchloride;n-butyllithium in diethyl ether;hexane;N,N-dimethyl-formamide

Steps:

2 Example 2
Example 2 Ethynyltrimethylsilane (5.0 g, 50.9 mmol) was dissolved in dry diethyl ether (50 ml), 1.6 M n-butyllithium in hexane(35.0 ml, 56.0 mmol) was added dropwise at 0°C under argon atmosphere. The mixture was stirred at the same temperature for 1h. DMF(3.72g, 50.9mmol) was dissolved in diethyl ether (20ml), and was added dropwise below 5°C for 30 min, then the mixture was stirred at room temperature for 2 h. The reaction was quenched by the addition of 2N hydrochloric acid, and the mixture was extracted with diethyl ether. The organic layer was washed with water, saturated sodium hydrogencarbonate solution, and brine in order, and dried over sodium sulfate. Purification by distillation (40-45°C/15mmHg) gave 3-(trimethylsilyl)propiol aldehyde (28%). Colorless oil ¹H-NMR (CDCl₃) δ:0.27 (9H, s), 9.17 (1H, s).

References:

Institute of Medicinal Molecular Design, Inc. EP1145718, 2001, A1

5272-36-6 Synthesis