[2-[dimethyl-[(E)-oct-1-enyl]silyl]phenyl]methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The same operation as in the production of the compound 1a was carried out except that 4-octyne (0.22 g, 2.0 mmol) was used instead of 0.55 g and 2.2 mmol of dimethyl[2-(2-tetrahydro-2H-pyranoxymethyl)phenylsilane (R2 and R3 in (5): methyl group) and 1-octyne, thereby (E)-(2-(hydroxymethyl)phenyl)dimethyl(4-octene-4-yl)silane (0.45 g, yield of 81%) as a colorless oil. Rf: 0.25 (hexane-ethyl acetate=10:1). 1H NMR (400 MHz, CDCl3) δ 7.54 (dd, J=7.2, 1.2 Hz, 1H), 7.47 (dd, J=7.2, 1.2 Hz, 1H), 7.40 (td, J=7.3, 1.4 Hz, 1H), 7.29 (m, 1H), 5.80 (t, J=7.2 Hz, 1H), 4.70 (s, 2H), 2.12-2.06 (m, 4H), 1.38 (m, 2H), 1.28-1.18 (m, 2H), 0.90 (t, J=7.4 Hz, 3H), 0.83 (t, J=7.2 Hz, 3H), 0.40 (s, 6H); 13C NMR (101 MHz, CDCl3) δ 146.6, 142.8, 140.2, 136.7, 135.3, 129.6, 128.0, 126.9, 65.2, 32.1, 30.8, 23.4, 22.6, 14.5, 14.0, −1.2; Anal. Calcd for C17H28Osi; C, 73.85; H, 10.21. Found: C, 73.67; H, 10.06.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The same operation as in the preparation of the compound 1a except that phenylacetylene (0.20 g, 2.0 mmol) was used instead of 0.55 g and 2.2 mmol of dimethyl[2-(2-tetrahydro-2H-pyranoxymethyl)phenylsilane (R2 and R3 in (5): methyl group) and 1-octyne, thereby obtaining (E)-(2-(hydroxymethyl)phenyl) dimethyl(2-phenylethenyl)silane (0.45 g, yield of 84%) as a colorless oil, Rf: 0.20 (hexane-ethyl acetate=10:1). 1H NMR (400 MHz, CDCl3) δ 7.62 (dd, J=7.4, 1.3 Hz, 1H), 7.51-7.41 (m, 4H), 7.37-7.27 (m, 4H), 6.97 (d, J=19.2 Hz, 1H), 6.67 (d, J=19.2 Hz, 1H), 4.79 (s, 2H), 0.52 (s, 6H); 13C NMR (101 MHz, CDCl3) δ 146.5, 145.2, 138.0, 136.4, 135.3, 130.0, 128.6, 128.3, 127.9, 127.8, 127.1, 126.5, 65.4, −1.2; Anal. Calcd for C17H20Osi; C, 76.07; H, 7.51. Found: C, 75.73; H, 7.55.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The same operation as in the preparation of the compound 1a except that phenylacetylene (0.20 g, 2.0 mmol) was used instead of 0.55 g and 2.2 mmol of dimethyl[2-(2-tetrahydro-2H-pyranoxymethyl)phenylsilane (R2 and R3 in (5): methyl group) and 1-octyne, thereby obtaining (E)-(2-(hydroxymethyl)phenyl) dimethyl(2-phenylethenyl)silane (0.45 g, yield of 84%) as a colorless oil, Rf: 0.20 (hexane-ethyl acetate=10:1). 1H NMR (400 MHz, CDCl3) δ 7.62 (dd, J=7.4, 1.3 Hz, 1H), 7.51-7.41 (m, 4H), 7.37-7.27 (m, 4H), 6.97 (d, J=19.2 Hz, 1H), 6.67 (d, J=19.2 Hz, 1H), 4.79 (s, 2H), 0.52 (s, 6H); 13C NMR (101 MHz, CDCl3) δ 146.5, 145.2, 138.0, 136.4, 135.3, 130.0, 128.6, 128.3, 127.9, 127.8, 127.1, 126.5, 65.4, −1.2; Anal. Calcd for C17H20Osi; C, 76.07; H, 7.51. Found: C, 75.73; H, 7.55.