Imidazole → 5-(t-Butyldimethylsiloxy)-3-pentyne

HRID 1197236Notes

Reaction equation

HRID 1197236 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].N1C=CN=[CH:15]1>CN(C=O)C>[O:5]([CH2:1][C:2]#[C:3][CH2:4][CH3:15])[Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

5

Reactant 3

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

Product 1

HCID 110198575-(t-Butyldimethylsiloxy)-3-pentyne

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-butyn-1-ol (g) (10.0 g) in DMF (80 ml) were added t-butyldimethylsilyl chloride (21.5 g) and imidazol (10.6 g), and the resultant mixture was kept at 35° C. for 7 hours. The reaction mixture was treated in the conventional manner and the obtained crude produce was distilled to give the title compound (h). Yield: 17.4 g (66%)

Workup

  1. additionThe reaction mixture was treated in the conventional manner
  2. customthe obtained crude
  3. customproduce
  4. distillationwas distilled

Sources & evidence

ORD record
ord-fda9fd1b20224985aa38ddb3cc811a77
Source dataset
uspto-grants-1992_05
Patent number
US05117042

Reaction notes

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