Imidazole → HCID 12851273, compound

HRID 1065144Notes

Reaction equation

HRID 1065144 reaction equation
[CH3:1][C:2]([OH:13])([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]#[CH:4].CN(C)C=O.N1C=CN=C1.[CH2:24]([Si:26](Cl)([CH2:29][CH3:30])[CH2:27][CH3:28])[CH3:25]>CCOCC.O>[CH3:1][C:2]([O:13][Si:26]([CH2:29][CH3:30])([CH2:27][CH3:28])[CH2:24][CH3:25])([CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:3]#[CH:4]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 13819ChlorotriethylsilaneHCID 4651150HCID 4651150, compound

Product 1

HCID 12851273HCID 12851273, compound

Reagents, catalysts & solvents 1

HCID 21584184Diethylether waterSolvent

Procedure

The hydroxyl group is protected by treating 3.6 parts of 3-methyl-3-hydroxy-5-phenyl-1-pentyne in 15 parts by volume of dimethylformamide successively with 3.5 parts of imidazole and 4.0 parts of triethylsilyl chloride and stirring this mixture for 1 hour at room temperature. The reaction mixture is poured into ether/water and the ethereal layer is washed with water three times, dried over anhydrous sodium sulfate, and then the ether is removed at reduced pressure. Distillation of the residual oil provides 3-methyl-5-phenyl-3-triethylsilyloxy-1-pentyne.

Workup

  1. washthe ethereal layer is washed with water three times
  2. dry with materialdried over anhydrous sodium sulfate
  3. customthe ether is removed at reduced pressure
  4. distillationDistillation of the residual oil

Sources & evidence

ORD record
ord-ae07eee35ada4632b67c66fffd3c46d2
Source dataset
uspto-grants-1982_05
Patent number
US04328355

Reaction notes

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