Potassium tert-butoxide → HCID 59227486, compound

HRID 1640056Notes

Reaction equation

HRID 1640056 reaction equation
[C:1]1([C:7]#[C:8][CH2:9][O:10][SiH:11]([CH3:13])[CH3:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.CC([O-])(C)C.[K+]>>[C:1]1([C:7]2[Si:11]([CH3:13])([CH3:12])[O:10][CH2:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

3

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 59227480HCID 59227480, compound

Product 1

HCID 59227486HCID 59227486, compoundYield 51.9%

Procedure

(3-Cyclohexenylprop-2-ynyloxy)dimethylsilane (2.77 g, 14.25 mmol) and KOtBu (0.160 g, 1.425 mmol) were used according to the general procedure. The brown oily crude reaction mixture was purified by flash chromatography using hexanes/Et2O (6:1) as eluant to produce 10e as a clear colorless oil (1.437 g, 7.394 mmol, 51.9%), which was used in Diels-Alder reactions without further purification. Analytical samples were prepared from this chromatographic compound (0.235 g, 1.209 mmol) by using a chromatotron (2.0 mm, silica gel) yielded the title compound as a colorless clear liquid in pure form (0.167 g, 0.859 mmol, 71.1%): Rf 0.34 (hexanes/Et2O, 8:1); 1H NMR (300 MHz, CDCl3) δ 6.49 (s, 1H, H-4), 5.61 (s, 1H, H-8), 4.64 (s, 1H, H-5), 2.04-2.26 (m, 4H, H-9, 12), 1.51-1.77 (m, 4H, H-10, 11), 0.32 (s, 6H, H-6); 13C NMR (300 MHz, CDCl3) δ 142.6 (C-3), 136.9 (C-4), 135.2 (C-7), 128.8 (C-8), 72.0 (C-5), 26.1 (C-9, 12), 22.6 (C-10/11), 22.4 (C-10/11), 0.74 (C-6); HRMS calcd for C11H18OSi (M+) 194.1127. found 194.1121.

Workup

  1. customThe brown oily crude reaction mixture
  2. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-d0875985921d4c719cce766776c713d4
Source dataset
uspto-grants-2012_02
Patent number
US08110695B2

Reaction notes

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