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

HRID 1769634Notes

Reaction equation

HRID 1769634 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].N1C=CN=C1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C([O-])(O)=O.[Na+]>CN(C=O)C>[O:5]([CH2:1][CH2:2][C:3]#[CH:4])[Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 135663-Butyn-1-OLHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 4304567(But-3-yn-1-yloxy)(tert-butyl)dimethylsilaneYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-butyne-1-ol (21.0 g, 0.3 mol) in 100 mL of DMF was added imidazole (41.3 g, 0.6 mol), followed by a solution of t-butyldimethylsilyl chloride (48.0 g, 0.32 mol) in 25 mL of DMF. After stirring at room temperature under Ar for 18 h, the reaction mixture was poured into 10% aqueous NaHCO3 (150 mL) and extracted with hexane (3×250 mL). The organic phase was washed (brine), dried (Na2SO4) and evaporated to give 1-(t-butyl dimethylsiloxy)-3-butyne (49.0 g, 89%) as a colourless oil: IR (neat) 3320, 2125 (w) , 1260, 1110, 840 cm-1 ; 1H NMR (CDCl3, 200 MHz) δ3.74 (t, J=7.2 Hz, 2H), 2.40 (dt, J=7.1, 2.6 Hz, 2H), 1.96 (t, J=2.6 Hz, 1H), 0.90 (s, 9 H), 0.07 (s, 6H).

Workup

  1. extractionextracted with hexane (3×250 mL)
  2. washThe organic phase was washed (brine)
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-d8e01ca980ed43d4894e395df3725da7
Source dataset
uspto-grants-1995_01
Patent number
US05382592

Reaction notes

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