Potassium tert-butoxide → HCID 59227484, compound

HRID 1640052Notes

Reaction equation

[CH3:1][C:2](=[CH2:14])[C:3]#[C:4][CH2:5][O:6][SiH:7]([CH:11]([CH3:13])[CH3:12])[CH:8]([CH3:10])[CH3:9].CC([O-])(C)C.[K+]>>[CH:8]([Si:7]1([CH:11]([CH3:13])[CH3:12])[C:3]([C:2]([CH3:1])=[CH2:14])=[CH:4][CH2:5][O:6]1)([CH3:10])[CH3:9]

Participants

Reactant 2

HCID 23665647Potassium tert-butoxide

HCID 59227504HCID 59227504, compound

Product 1

HCID 59227484HCID 59227484, compound

Procedure

(4-Methylpent-4-en-2-ynyloxy)diisopropylsilane (1.662 g, 7.90 mmol) and KOtBu (0.092 g, 0.8199 mmol) were used according to the general procedure mentioned above. The light brown clear solution was subjected to column chromatography and yielded 8a as colorless, clear liquid (1.192 g, 5.666 mmol, 71.7%): Rf0.37 (hexanes/Et2O, 15:1); 1H NMR (500 MHz, CDCl3) δ 6.68 (t, J=1.9 Hz, 1H, H-4), 4.99 (s, 1H, H-9), 4.80 (s, 1H, H-9), 4.63 (dd, J=1.9, 0.9 Hz, 2H, H-5), 1.94 (s, 3H, H-10), 1.09-1.19 (m, 2H, H-6), 1.04 (d, J=7.3 Hz, 6H, H-7), 0.99 (d, J=7.3 Hz, 6H, H-7); 13C NMR (300 MHz, CDCl3) δ 142.4 (C-4), 142.1 (C-8), 139.8 (C-3), 116.3 (C-9), 72.7 (C-5), 20.6 (C-10), 17.3 (C-7), 17.0 (C-7), 13.3 (C-6); Anal. calcd for C12H22OSi: C, 68.51; H, 10.54. Found: C, 68.24; H, 10.61.

Sources & evidence

ORD record: ord-16cf6f07d9ad4b99bee25579f538cef0
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110695B2

Reaction notes

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