Triethylamine → HCID 59227494, compound

HRID 1640051Notes

Reaction equation

[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

Participants

Reactant 4

HCID 8471Triethylamine

HCID 218852-Dimethylaminopyridine

HCID 2758383Chlorodi(isopropyl)silane

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

Product 1

HCID 59227494HCID 59227494, compoundYield 52.7%

Procedure

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.

Sources & evidence

ORD record: ord-edb2cd877aca47308c21e64bbbb845b3
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110695B2

Reaction notes

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