Imidazole → 4-((Tert-butyldimethylsilyl)oxy)but-2-yn-1-ol

HRID 891037Notes

Reaction equation

[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCCCCC.[CH2:15]([OH:19])[C:16]#[C:17][CH3:18].N1C=CN=C1.CN(C)C=[O:28]>CCOCC>[Si:1]([O:19][CH2:15][C:16]#[C:17][CH2:18][OH:28])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 22 °C

Procedure

A solution of 175 g of tert-butyldimethylsilyl chloride in 100 ml of a 1:1 mixture that consists of hexane and dimethylformamide is slowly added in drops at 0° C. under nitrogen to a solution of 100 g of 2-butin-1-ol and 158 g of imidazole in 300 ml of dimethylformamide, and it is stirred for 2 hours at 0° C. and for 16 hours at 22° C. The reaction mixture is diluted with 2.5 l of ether, washed once with water, once with 5% sulfuric acid, once with water, once with saturated sodium bicarbonate solution and washed neutral with semi-saturated sodium chloride solution. After drying on sodium sulfate and filtration, it is concentrated by evaporation in a vacuum. The residue that is thus obtained is purified by chromatography on silica gel. With hexane/0–40% ether, 74.3 g of the title compound is obtained as a colorless oil.

Workup

washwashed once with water, once with 5% sulfuric acid, once with water, once with saturated sodium bicarbonate solution
washwashed neutral with semi-saturated sodium chloride solution
customAfter drying on sodium sulfate and filtration, it
concentrationis concentrated by evaporation in a vacuum
customThe residue that is thus obtained
customis purified by chromatography on silica gel

Sources & evidence

ORD record: ord-5ab7c7dd027846f3b88a090e622a767a
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07001916B1

Reaction notes

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