Imidazole → {[1-(4-Fluorophenoxy)but-3-yn-2-yl]oxy}(trimethyl)silane

HRID 1395165Notes

Reaction equation

HRID 1395165 reaction equation
[OH:1][CH:2]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)[C:3]#[CH:4].N1C=CN=C1.Cl[Si:20]([CH3:23])([CH3:22])[CH3:21].CCCCCC>CN(C)C=O>[F:13][C:10]1[CH:9]=[CH:8][C:7]([O:6][CH2:5][CH:2]([O:1][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:3]#[CH:4])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 8058HexaneHCID 127862161-(4-Fluorophenoxy)but-3-yn-2-ol

Product 1

HCID 12786217{[1-(4-Fluorophenoxy)but-3-yn-2-yl]oxy}(trimethyl)silaneYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. solution of 10 g (55 mmoles) of 3-hydroxy-4-p-fluorophenoxy-1-butyne (Example 157) in 75 ml of dry dimethylformamide and 88 g (130 mmoles) of imidazole is added dropwise, with stirring, 7.5 g (68 mmoles) of chlorotrimethylsilane. The mixture, while under an argon atmosphere, is stirred at room temperature for 18 hours, and then poured into 150 ml of hexane and 100 ml of ice-water. The organic phase is separated, washed with 50 ml of a brine solution, dried with magnesium sulfate, and evaporated under vacuum. This crude product is distilled under vacuum at 0.1 mm (bp 73°-75° C.), to give 12.2 g (91%) of the subject compound as a colorless oily liquid.

Workup

  1. stirringThe mixture, while under an argon atmosphere, is stirred at room temperature for 18 hours
  2. customThe organic phase is separated
  3. washwashed with 50 ml of a brine solution
  4. dry with materialdried with magnesium sulfate
  5. customevaporated under vacuum
  6. distillationThis crude product is distilled under vacuum at 0.1 mm (bp 73°-75° C.)

Sources & evidence

ORD record
ord-beb467c574974cab92a6e4fc2d401d99
Source dataset
uspto-grants-1980_05
Patent number
US04202822

Reaction notes

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