Imidazole → 5-(t-Butyldimethylsilyloxy)pent-1-yne

HRID 2358470Notes

Reaction equation

HRID 2358470 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][OH:6].N1C=CN=C1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].O>CN(C=O)C>[O:6]([CH2:5][CH2:4][CH2:3][C:2]#[CH:1])[Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 793464-Pentyn-1-ol

Product 1

HCID 108673065-(t-Butyldimethylsilyloxy)pent-1-yneYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.00 g (59.4 mmol) of pent-1-yn-5-ol were dissolved in 50 ml of dry DMF, and 10.10 g (149 mmol, 2.5 eq.) of imidazole and 9.40 g (62.4 mmol, 1.1 eq.) of TBS-Cl were added. After 12 hours of stirring at RT, 250 ml of water were added and the mixture was extracted with 3×150 ml of MTBE. The organic phase was washed 3× with in each case 100 ml of water and then dried over MgSO4. Purification by column chromatography gave 11.10 g (53.5 mmol, 90%) of 5-(tert-butyldimethylsiloxy)pent-1-yne as a colorless oil.

Workup

  1. extractionthe mixture was extracted with 3×150 ml of MTBE
  2. washThe organic phase was washed 3× with in each case 100 ml of water
  3. dry with materialdried over MgSO4
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-92218f93f1354884b02ac5f4a9a6c25b
Source dataset
uspto-grants-2010_07
Patent number
US07763740B2

Reaction notes

Loading…