Triethylamine → (3,6-Dimethylhepta-1,6-dien-4-yn-3-yloxy)diisopropylsilane

HRID 1640050Notes

Reaction equation

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

Participants

Reactant 4

HCID 8471Triethylamine

HCID 218852-Dimethylaminopyridine

HCID 2758383Chlorodi(isopropyl)silane

HCID 592274973,6-Dimethylhepta-1,6-dien-4-yn-3-ol

Product 1

HCID 59227496(3,6-Dimethylhepta-1,6-dien-4-yn-3-yloxy)diisopropylsilane

Procedure

3,6-Dimethylhepta-1,6-dien-4-yn-3-ol (6d) (1.523 g, 11.18 mmol), triethylamine (1.2 g, 11.86 mmol), dimethylaminopyridine (0.153 g, 1.275 mmol) and diisopropylchlorosilane (1.657 g, 10.99 mmol) were used according to the general procedure. The brown, clear crude product was purified by column chromatography to produce the title compound (7d) as a clear colorless solution (2.641 g, 10.54 mmol, 96.3%): Rf 0.91 (hexanes/Et2O, 4:1); 1H NMR (300 MHz, CDCl3) δ 5.92 (dd, J=17.0, 10.2 Hz, 1H, H-2), 5.44 (d, J=17.0 Hz, 1H, H-1), 5.28 (bs, 1H, H-7), 5.22 (p, J=1.5 Hz, 1H, H-7), 5.07 (d, J=10.2 Hz, 1H, H-1), 4.36 (s, 1H, H-10), 1.89 (s, 3H, H-8), 1.56 (s, 3H, H-9), 0.95-1.14 (m, 14H, H-11, 12); 13C NMR (300 MHz, CDCl3) δ 142.6 (C-2), 126.4 (C-6), 121.6 (C-7), 112.8 (C-1), 89.9 (C-4), 86.9 (C-5), 70.5 (C-3), 31.6 (C-9), 23.3 (C-8), 17.6 (C-12), 17.55 (C-12), 17.53 (C-12), 12.7 (C-11), 12.6 (C-11); HRMS calcd for C15H26OSi (M+) 250.1753. found 250.1744.

Workup

customThe brown, clear crude product was purified by column chromatography

Sources & evidence

ORD record: ord-c40efca9de1d43f191f6069d53730d49
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110695B2

Reaction notes

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