Imidazole → HCID 11139434, compound

HRID 1284969Notes

Reaction equation

HRID 1284969 reaction equation
[C:1]1([CH:7]([OH:10])[C:8]#[CH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1.O>CN(C)C=O>[O:10]([CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]#[CH:9])[Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 20155alpha-EthynylbenzenemethanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11139434HCID 11139434, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.0 g (37.9 mmol) of 1-phenyl-2-propyne-1-ol in 20 ml of dimethyl formamide were added 6.9 g (45.8 mmol) of t-butyl dimethylsilyl chloride and 6.2 g (91.1 mmol) of imidazole, and the resulting mixture was stirred at room temperature for 3 hours, 50 ml of water was added and the mixture was extracted with a pentane-ether (1:1) mixture (4×30 ml). The organic layer was washed with water (30 ml) and saturated brine, dried over anhydrous magnesium sulfate (30 mg) and thereafter concentrated. The residue was purified by column chromatography (silica gel 100 g, cyclohexane-ethyl acetate) and further distilled (dp 98° C./1 mm Hg) to give 5.7 g (24.7 mmol, 65%) of the subject compound.

Workup

  1. extractionthe mixture was extracted with a pentane-ether (1:1) mixture (4×30 ml)
  2. washThe organic layer was washed with water (30 ml) and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate (30 mg)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (silica gel 100 g, cyclohexane-ethyl acetate)
  6. distillationfurther distilled (dp 98° C./1 mm Hg)

Sources & evidence

ORD record
ord-183a252ccd4f49dc95c3f1500c86c099
Source dataset
uspto-grants-1986_01
Patent number
US04564620

Reaction notes

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