Triethylamine → HCID 59227504, compound

HRID 1640049Notes

Reaction equation

[CH3:1][C:2](=[CH2:7])[C:3]#[C:4][CH2:5][OH:6].CN(C1C=CC=CN=1)C.C(N(CC)CC)C.[CH:24]([SiH:27]([CH:29]([CH3:31])[CH3:30])Cl)([CH3:26])[CH3:25]>>[CH3:7][C:2](=[CH2:1])[C:3]#[C:4][CH2:5][O:6][SiH:27]([CH:29]([CH3:31])[CH3:30])[CH:24]([CH3:26])[CH3:25]

Participants

Reactant 4

HCID 8471Triethylamine

HCID 218852-Dimethylaminopyridine

HCID 2758383Chlorodi(isopropyl)silane

HCID 108878354-methyl-4-penten-2-yn-1-ol

Product 1

HCID 59227504HCID 59227504, compoundYield 89.5%

Procedure

4-Methylpent-4-en-2-yn-1-ol (2.0 g, 20.80 mmol), dimethylaminopyridine (0.252 g, 2.1 mmol), triethylamine (2.126 g, 21.01 mmol) and diisopropylchlorosilane (3.135 g, 20.80 mmol) were used according to the general procedure described above. The resulting clear, light yellow colored crude compound was purified by flash chromatography to yield pure product (3.914 g, 18.62 mmol, 89.5%) as clear colorless solution: Rf 0.82 (hexanes/Et2O, 9:1); 1H NMR (500 MHz, CDCl3) δ 5.28 (bs, 1H, H-5), 5.22 (bs, 1H, H-5), 4.49 (s, 1H, H-1), 4.21 (s, 1H, H-7), 1.88 (s, 3H, H-6), 0.74-1.37 (m, 14H, H-8, 9); 13C NMR (300 MHz, CDCl3) δ 126.5 (C-4), 121.8 (C-5), 86.5 (C-3), 86.3 (C-2), 54.3 (C-1), 23.2 (C-6), 17.3 (C-9), 17.2 (C-9), 12.3 (C-8); Anal. calcd for C12H22OSi: C, 68.51; H, 10.54. Found: C, 68.32; H, 10.73.

Workup

customThe resulting clear, light yellow colored crude compound was purified by flash chromatography

Sources & evidence

ORD record: ord-e813653e3be0407c81a386796561b171
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110695B2

Reaction notes

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