Triethylamine → HCID 59227494、化合物

反応式

[C:1]1([C:7]#[C:8][CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[CH:27]([SiH:30]([CH:32]([CH3:34])[CH3:33])Cl)([CH3:29])[CH3:28]>>[C:1]1([C:7]#[C:8][CH2:9][O:10][SiH:30]([CH:32]([CH3:34])[CH3:33])[CH:27]([CH3:29])[CH3:28])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

参加物

反応物 4

HCID 8471Triethylamine

HCID 218852-Dimethylaminopyridine

HCID 2758383Chlorodi(isopropyl)silane

HCID 127701823-(Cyclohex-1-en-1-yl)prop-2-yn-1-ol

生成物 1

HCID 59227494HCID 59227494、化合物収率 52.7%

実験手順

3-Cyclohexenylprop-2-yn-1-ol (61) (1.236 g, 12.86 mmol), triethylamine (1.30 g, 12.85 mmol), dimethylaminopyridine (0.152 g, 1.267 mmol) and diisopropylchlorosilane (1.918 g, 12.73 mmol) were used to yield compound 7e (1.680 g, 6.71 mmol, 52.7%) as a colorless, clear oily substance after purification by flash chromatography: Rf 0.85 (hexanes/Et2O, 4:1); 1H NMR (500 MHz, CDCl3) δ 6.08 (h, J=1.8 Hz, 1H, H-5), 4.48 (s, 2H, H-1), 4.20 (s, 2H, H-10), 1.98-2.17 (m, 4H, H6-9), 1.49-1.71 (m, 4H, H6-9), 0.96-1.12 (m, 14H, H-11, 12). 13C NMR (300 MHz, CDCl3) δ 134.8 (C-5), 120.3 (C-4), 87.1 (C-2/3), 84.4 (C-2/3), 54.3 (C-1), 29.0 (C6-9), 25.6 (C6-9), 22.2 (C6-9), 21.5 (C6-9), 17.3 (C-12), 17.2 (C-12), 12.3 (C-11); HRMS calcd for C15H26NaOSi (M+Na)+ 273.1651. found 273.1639.