TRANS-3-(TRIMETHYLSILYL)ALLYL ALCOHOL

Uses

trans-3-(Trimethylsilyl)allyl alcohol is suitable for use in the preparation of 1-iodo-3-trimethylsilyl-2-propene, via mesylation followed by iodide displacement.

General Description

trans-3-(Trimethylsilyl)allyl alcohol is a 3-silyl allyl alcohol.

Synthesis

General procedure for the synthesis of trans-3-(trimethylsilyl)allylpropanol from trimethylsilylpropargyl alcohol: The alcohol prepared in Example 40 (1.54 g, 12 mmol, 1 eq.) was dissolved in anhydrous THF (12 mL) under argon protection and slowly added dropwise to a suspension of LiAlH4 (0.7 g, 18 mmol, 1.5 eq.) in THF (15 mL) , stirred at room temperature. Subsequently, the reaction mixture was heated to reflux for 4 hours. Upon completion of the reaction, the reaction was quenched with saturated aqueous NaHCO3 and aqueous NH4Cl. The reaction mixture was extracted with Et2O (3 × 50 mL) and the organic layers were combined, washed with brine and dried over MgSO4. The solvent was removed by concentration under reduced pressure to give the target product (1.39 g, 10.6 mmol, 89% yield) as a colorless liquid. The structure of the product was determined by 1H NMR (400 MHz, CDCl3) δ 6.19 (1H, m, H-3), 5.93 (1H, dt, J2-3 = 18.8 Hz, J2-4 = 1.45 Hz, H-2), 4.18 (2H, dd, J4-3 = 2.72, J4-2 = 1.45, H-4), 1.56 (1H, s, H-5) , 0.09 (9H, s, H-1); 13C NMR (100 MHz, CDCl3) δ 144.8 (C-3), 129.5 (C-2), 65.5 (C-4), -1.37 (C-5); confirmed by IR (pure, cm-1) 3331 (b, OH), 1622 (s, C=C).

References

[1] Journal of Organic Chemistry, 1988, vol. 53, # 20, p. 4682 - 4693
[2] Journal of the American Chemical Society, 1989, vol. 111, # 24, p. 8834 - 8841
[3] Tetrahedron, 1996, vol. 52, # 21, p. 7487 - 7510
[4] Chinese Journal of Chemistry, 2018, vol. 36, # 10, p. 916 - 920
[5] Patent: US2007/142632, 2007, A1. Location in patent: Page/Page column 26