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

HRID 1395298Notes

Reaction equation

HRID 1395298 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 9) 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, p.m.r. 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, p.m.r

Sources & evidence

ORD record
ord-e520edb7838d4419ab83afc87291ac15
Source dataset
uspto-grants-1980_05
Patent number
US04202989

Reaction notes

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