Imidazole → t-Butyl[(2,2-dimethylpent-4-yn-1-yl)oxy]dimethylsilane

HRID 1875374Notes

Reaction equation

N1C=CN=C1.[C:6]([Si:10]([CH3:13])([CH3:12])Cl)([CH3:9])([CH3:8])[CH3:7].[CH3:14][C:15]([CH3:21])([CH2:18][C:19]#[CH:20])[CH2:16][OH:17]>CN(C=O)C>[C:6]([Si:10]([O:17][CH2:16][C:15]([CH3:21])([CH3:14])[CH2:18][C:19]#[CH:20])([CH3:13])[CH3:12])([CH3:9])([CH3:8])[CH3:7]

Participants

Conditions

Temperature: 22 °C

Procedure

Imidazole (58.3 g, 857 mmol) and t-butydimethylchlorosilane (64.6 g, 429 mmol) were added to a stirred solution of 2,2-dimethylpent-4-yn-1-ol (43.7 g, 390 mmol) in DMF (195 mL), then the solution was stirred at 22° C., under N2, for 20 hours. The reaction solution was extracted with ether (3×300 mL), washed with water (100 mL), brine (75 mL), dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel 60 (330 g), eluting with hexane, to give the title product. 1H NMR (400 MHz, CDCl3) δ 3.29 (s, 2H); 2.10 (d, J=2.8 Hz, 2H); 1.91 (t, J=2.6 Hz, 1H); 0.90 (s, 6H); 0.86 (s, 9H); 0.00 (s, 6H) ppm.

Workup

extractionThe reaction solution was extracted with ether (3×300 mL)
washwashed with water (100 mL), brine (75 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was chromatographed on silica gel 60 (330 g)
washeluting with hexane

Sources & evidence

ORD record: ord-03581ad096eb46b7b377b43a2fbffcbd
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309540B2

Reaction notes

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