Imidazole → (But-3-yn-1-yloxy)(tert-butyl)dimethylsilane

HRID 902620Notes

Reaction equation

HRID 902620 reaction equation
[OH:1][CH2:2][CH2:3][C:4]#[CH:5].N1C=CN=C1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]>CN(C=O)C.O>[Si:11]([O:1][CH2:2][CH2:3][C:4]#[CH:5])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 135663-Butyn-1-OLHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 4304567(But-3-yn-1-yloxy)(tert-butyl)dimethylsilaneYield 89.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-hydroxybut-3-yne (2.0 g, 0.028 mol) and imidazole (2.9 g, 0.043 mol) in DMF (5 ml) was treated with t-butyldimethylsilyl chloride (6.4 g, 0.043 mol). After 24 hr. at RT, the reaction was diluted with water and extracted with diethyl ether. The organic extracts were washed with water, dried, evaporated, and the volatile organics were removed by vacuum to afford the title compound as an oil (4.6 g, 89%). 1H NMR (400 MHz, CDCl3): δ 3.67 (t, J=7.1 Hz, 2H), 2.32 (m, 2H), 1.88 (s, 1H), 0.82 (s, 9H), 0.00 (s, 6H).

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic extracts were washed with water
  3. customdried
  4. customevaporated
  5. customthe volatile organics were removed by vacuum

Sources & evidence

ORD record
ord-a6f6f63e4b4b4ac98580f50ea7b1b8b6
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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