Imidazole → [(4-Cyclopropyloct-1-yn-4-yl)oxy](trimethyl)silane

HRID 261390Notes

Reaction equation

HRID 261390 reaction equation
[CH:1]1([C:4]([OH:12])([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:5][C:6]#[CH:7])[CH2:3][CH2:2]1.N1C=CN=C1.Cl[Si:19]([CH3:22])([CH3:21])[CH3:20]>CN(C)C=O>[CH:1]1([C:4]([O:12][Si:19]([CH3:22])([CH3:21])[CH3:20])([CH2:8][CH2:9][CH2:10][CH3:11])[CH2:5][C:6]#[CH:7])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 130787514-Cyclopropyl-4-hydroxy-1-octyne

Product 1

HCID 13078752[(4-Cyclopropyloct-1-yn-4-yl)oxy](trimethyl)silane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 27.8 g of 4-cyclopropyl-4-hydroxy-1-octyne (Example 190) and 33.3 g of imidazole in 130 ml of dimethylformamide at 5° C. is added 24 ml of chlorotrimethylsilane during 5 minutes. The solution is stirred at ambient temperature for 17 hours and then partitioned with 600 ml of hexane and 250 ml of ice water. The hexane phase is separated and washed successively with water and brine. The solution is dried over magnesium sulfate and evaporated to give a liquid, pmr spectrum (CDCl3): δ 0.12 (singlet, trimethylsiloxy group), 2.02 (triplet, HC≡C), and 2.45 (doublet, C≡CH2).

Workup

  1. custompartitioned with 600 ml of hexane and 250 ml of ice water
  2. customThe hexane phase is separated
  3. washwashed successively with water and brine
  4. dry with materialThe solution is dried over magnesium sulfate
  5. customevaporated
  6. customto give a liquid, pmr spectrum (CDCl3)

Sources & evidence

ORD record
ord-e8bdc07f3e3d4a3ebafc525efa4e6082
Source dataset
uspto-grants-1979_08
Patent number
US04165331

Reaction notes

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